MODIFIED COUMARINS. 19. SYNTHESIS OF NEOFLAVONE D-GLYCOPYRANOSIDES
|
|
- Allyson Lyons
- 6 years ago
- Views:
Transcription
1 Chemistry of Natural Compounds, Vol. 41, No. 6, 2005 MDIFIED CUMARINS. 19. SYNTHESIS F NEFLAVNE D-GLYCPYRANSIDES Ya. L. Garazd, 1 M. M. Garazd, 2 and V. P. Khilya 1 UDC Neoflavone β-d-glucopyranosides, β-d-galactopyranosides, β-d-xylopyranosides, and α-darabinopyranosides were synthesized by Michael condensation of potassium salts of 7-hydroxy-4- arylcoumarins with acetobromosugars followed by deacetylation of the resulting peracetates. Key words: coumarins, neoflavones, 4-arylcoumarins, glycosides, glycosylation. More than 130 neoflavones with the 4-phenylcoumarin structure have been isolated from natural sources [1, 2]. Among the natural neoflavones are -glycosides with the carbohydrate at various positions of the coumarin. Examples of these are serratin 7-β-glucoside (1) isolated from Passiflora serratodigitata [3], 6--β-D-galactopyranosyldalbergin (2) isolated from Hesperethusa crenulata [4], and 5--(6 -acetyl-β-d-glucopyranosyl)-7,3,4 -trihydroxy-4-phenylcoumarin (3) produced by Hintonia latiflora [5]. The goal of our work was to synthesize -D-glycopyranosides of 7-hydroxy-4-arylcoumarins. 7-Hydroxy-4-arylcoumarins 4-7 that were needed for further transformations were prepared in high yields by Pechmann condensation of ethylbenzoylacetate and ethyl-4-methoxybenzoylacetate with polyphenols (resorcinol and 2-methylresorcinol) in the presence of conc. H 2 S 4 [6, 7]. The -glycopyranosides of the 7-hydroxy-4-arylcoumarins were synthesized using a method based on the reaction of a glycosyl donor and the potassium salts of the hydroxycoumarins in aqueous acetone with cooling (0 C) (modified Michael method [8, 9]) that was successfully used to synthesize a similar class of compounds [10]. The condensation of the potassium salts of 4-7 and acetobromosugars was carried out in concentrated aqueous acetone solution. Concentrated solutions of the phenolates of 4-7 were prepared using equivalent amounts of coumarins, KH solution (10%), and twice (relative to the volume of base solution) the amount of acetone. The glycosyl donors in these syntheses were the D-acetobromoglycopyranoses α-acetobromoglucose (Ac 4 GlupBr), α-acetobromogalactose (Ac 4 GalpBr), β-acetobromoarabinose (Ac 3 ArapBr), and α-acetobromoxylose (Ac 3 XylpBr). The syntheses produced in 36-52% yields the -peracetates of glucopyranosides 8-10, galactopyranosides 11-14, xylopyranoside 15, and arabinopyranoside 16, all of which have the sugar at the 7-position of the neoflavone. The structures of the prepared glycosides and the configurations of their anomeric centers were confirmed unambiguously by PMR spectroscopy. The PMR spectra of 8-16 contained signals for four (for glucosides and galactosides) or three (for arabinosides and xylosides) acetyl groups at ppm and for the carbohydrates and aglycons. The PMR spectra of 8-10 exhibited a doublet at ppm with SSCC J = Hz for H-1 of the carbohydrate ring. A SSCC of this magnitude for H-1 and H-2 in carbohydrates is consistent with their trans-diaxial position in the ring [11]. Together with the chemical shift of H-1, this confirmed the β-configuration of the glucopyranosides. The CH 2-6 methylene protons of the glucosides were chemically nonequivalent and formed together with H-5 a group of signals near 4 ppm. The methylene protons resonated as two doublets of doublets at and ppm with SSCC J = and J = and J = and , respectively. 1) Taras Shevchenko Kiev National University, 01033, Ukraine, Kiev, ul. Vladimirskaya, 64; 2) Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 02094, Ukraine, Kiev, ul. Murmanskaya, 1, gmm@i.com.ua. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp , November-December, riginal article submitted ctober 3, /05/ Springer Science+Business Media, Inc. 663
2 H Ac 4 GlupBr, KH H 2 -CH 3 CCH 3 Ac Ac Ac Ac MeNa MeH H H H H 4-7 R 8-10 R R Ac 4 GalpBr, KH H 2 -CH 3 CCH 3 Ac Ac Ac MeNa MeH H H H Ac H R R 4, 8, 11, 17, 20: R = = H; 5, 9, 12, 18, 21: = Me, R = H; 6, 10, 13, 19, 22: = H, R = CH 3 7, 14, 23: = Me, R = CH 3 H 4 Ac 3 XylpBr, KH MeNa H 2 -CH 3 CCH Ac H 3 MeH Ac Ph H Ac H Ac H Ac 3 ArapBr, KH MeNa H 2 -CH 3 CCH Ac MeH H 3 Ac H Ph 16 Ph 25 Ph PMR spectra of contained a doublet for H-1 of the carbohydrate at ppm with SSCC J = Hz. This was consistent with the β-configuration of the prepared galactopyranosides. In contrast with the glucopyranosides, the CH 2-6 methylene protons of the galactopyranosides appeared as a complicated multiplet at ppm. A doublet for H-1 in the PMR spectrum of triacetylxyloside 15 at 5.26 ppm with SSCC J = 7.2 Hz is consistent with the β-configuration of the anomeric center. The CH 2-5 methylene protons resonated as two doublet of doublets at 3.59 and 4.22 ppm with SSCC J = 12.0, J = 6.0 and J = 12.0, J = 2.1 Hz, respectively. The presence in the PMR spectrum of 16 of a doublet for H-1 at 5.20 ppm with SSCC J = 6.0 Hz confirmed that H-1 and H-2 were trans-diaxial. For a D-triacetylarabinoside, this occurs exclusively for the α-anomer, i.e., the arabinoside had the α-configuration. The CH 2-5 methylene protons resonated as two doublets of doublets at 3.83 and 4.15 ppm with SSCC J = 12.0, J = 2.1 and J = 12.0, J = 6.0 Hz, respectively. The IR spectra of 8-16 contained two bands at cm -1 that were characteristic of acetyl C= and coumarin ring stretching vibrations, respectively. D-Glycopyranosides with free hydroxyls were prepared in high yields by deacetylation of tetra- and tri-acetylglycopyranosides 8-16 using a modified Zemplen method (NaMe in absolute MeH). The PMR spectra of the synthesized glycosides contained signals for the carbohydrate and aglycon fragments and lacked signals for the acetyls in the starting peracetates. The presence in the PMR spectra of a doublet for anomeric H-1 with a typical SSCC confirmed that the 1,2-trans-diaxial orientation of H-1 and H-2 had been retained. The IR spectra of the glycopyranosides contained two bands at and cm -1 that were typical of hydroxyls and C= of the coumarin ring, respectively. 664
3 EXPERIMENTAL The course of reactions and the purity of products were monitored by TLC on Merck 60 F254 plates with elution by CHCl 3 :CH 3 H (9:1). Melting points were determined on a Kofler block. IR spectra were recorded on a Nicolet FTIR Nexus 475 spectrometer; PMR spectra, on Varian VXR-300 and Varian Mercury 400 spectrometers at 300 and 400 MHz, respectively, relative to TMS (internal standard). Elemental analyses agreed with those calculated. The syntheses of 7-hydroxy-4-arylcoumarins 4-7 have been published [6, 7]. Peracetylpyranosylbromides were prepared as before [12, 13]. 7-Peracetylglycopyranosyloxy-4-arylchromen-2-ones A solution of 7-hydroxycoumarin (4-7, 10 mmol) in acetone (10 ml) and KH solution (5.6 ml, 10%) was stirred vigorously and cooled (0 C) for 30 min, treated in portions with stirring over 1 h with the appropriate peracetylpyranosylbromide (10 mmol), stirred for 4 h with cooling (0 C), left overnight at room temperature, diluted with CHCl 3 (50 ml), and worked up in a separatory funnel with KH solution (1 N, 2 50 ml) and water (50 ml). Acidification of the combined alkaline extracts regenerated unreacted hydroxycoumarin. The organic layer was dried over anhydrous MgS 4 and evaporated in a rotary evaporator. The oily product was crystallized from propan-2-ol. 7-(2,3,4,6-Tetra--acetyl-β-D-glucopyranosyloxy)-4-phenylchromen-2-one (8), yield 42%, C 29 H 28 12, mp C. IR spectrum (KBr, cm -1 ): 1756, 1696, 1612, 1568, 1444, 1376, 1220, PMR spectrum (400 MHz, CDCl 3, δ, ppm, J/Hz): 2.05, 2.06, 2.07, 2.13 (12H, four s, four CH 3 C), 3.93 (1H, m, H-5 ), 4.19 (1H, dd, J = 12.4, J = 2.4, H-6 α), 4.31 (1H, dd, J = 12.4, J = 5.6, H-6 β), 5.17 (1H, d, J = 7.6, H-1 ), 5.19 (1H, m, H-4 ), (2H, m, H-2, H-3 ), 6.28 (1H, s, H-3), 6.86 (1H, dd, J = 2.4, J = 8.8, H-6), 7.03 (1H, d, J = 2.4, H-8), 7.41 (1H, d, J = 8.8, H-5), 7.43 (2H, m, H-2, H-6 ), 7.53 (3H, m, H-3, H-4, H-5 ). 7-(2,3,4,6-Tetra--acetyl-β-D-glucopyranosyloxy)-8-methyl-4-phenylchromen-2-one (9), yield 46%, C 30 H 30 12, mp C. IR spectrum (KBr, cm -1 ): 1756, 1692, 1606, 1452, 1374, 1248, PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.05, 2.06, 2.08 (12H, three s, four CH 3 C), 2.31 (3H, s, CH 3-8), 3.87 (1H, m, H-5 ), 4.17 (1H, dd, J = 12.0, J = 2.4, H-6 α), 4.30 (1H, dd, J = 12.0, J = 5.7, H-6 β), 5.12 (1H, d, J = 7.8, H-1 ), 5.19 (1H, t, J = 9.6, H-4 ), (2H, m, H-2, H-3 ), 6.28 (1H, s, H-3), 6.91 (1H, dd, J = 8.7, H-6), 7.29 (1H, d, J = 8.7, H-5), 7.43 (2H, m, H-2, H-6 ), 7.50 (3H, m, H-3, H-4, H-5 ). 7-(2,3,4,6-Tetra--acetyl-β-D-glucopyranosyloxy)-4-(4-methoxyphenyl)chromen-2-one (10), yield 49%, C 30 H 30 13, mp C. IR spectrum (KBr, cm -1 ): 1758, 1698, 1610, 1512, 1424, 1376, 1216, 1156, 1120, PMR spectrum (400 MHz, CDCl 3, δ, ppm, J/Hz): 2.05, 2.07, 2.13 (12H, three s, four CH 3 C), 3.89 (3H, s, CH 3-4 ), 3.93 (1H, m, H-5 ), 4.19 (1H, dd, J = 12.4, J = 2.0, H-6 α), 4.31 (1H, dd, J = 12.4, J = 6.0, H-6 β), 5.18 (1H, d, J = 7.2, H-1 ), 5.19 (1H, m, H-4 ), (2H, m, H-2, H-3 ), 6.25 (1H, s, H-3), 6.86 (1H, dd, J = 2.4, J = 8.8, H-6), 7.01 (1H, d, J = 2.4, H-8), 7.04 (2H, d, J = 8.4, H-3, H-5 ), 7.39 (2H, d, J = 8.4, H-2, H-6 ), 7.48 (1H, d, J = 8.8, H-5). 7-(2,3,4,6-Tetra--acetyl-β-D-galactopyranosyloxy)-4-phenylchromen-2-one (11), yield 36%, C 29 H 28 12, light yellow oil. PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.06, 2.12, 2.18 (12H, three s, four CH 3 C), (3H, m, H-5, CH 2-6 ), 5.05 (1H, d, J = 8.1, H-1 ), 5.15 (1H, dd, J = 3.3, J = 8.1, H-3 ), 5.45 (1H, d, J = 3.3, H-4 ), 5.57 (1H, dd, J = 8.1, J = 8.1, H-2 ), 6.28 (1H, s, H-3), 6.86 (1H, dd, J = 2.4, J = 8.7, H-6), 7.03 (1H, d, J = 2.4, H-8), 7.41 (1H, d, J = 8.7, H-5), 7.43 (2H, m, H-2, H-6 ), 7.53 (3H, m, H-3, H-4, H-5 ). 7-(2,3,4,6-Tetra--acetyl-β-D-galactopyranosyloxy)-8-methyl-4-phenylchromen-2-one (12), yield 46%, C 30 H 30 12, mp C. IR spectrum (KBr, cm -1 ): 1758, 1696, 1604, 1444, 1370, 1222, PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.04, 2.09, 2.21 (12H, three s, four CH 3 C), 2.32 (3H, s, CH 3-8), (3H, m, H-5, CH 2-6 ), 5.09 (1H, d, J = 8.1, H-1 ), 5.15 (1H, dd, J = 3.3, J = 8.1, H-3 ), 5.48 (1H, d, J = 3.3, H-4 ), 5.60 (1H, dd, J = 8.1, J = 8.1, H-2 ), 6.28 (1H, s, H-3), 6.92 (1H, d, J = 8.7, H-6), 7.29 (1H, d, J = 8.7, H-5), 7.43 (2H, m, H-2, H-6 ), 7.52 (3H, m, H-3, H-4, H-5 ). 665
4 7-(2,3,4,6-Tetra--acetyl-β-D-galactopyranosyloxy)-4-(4-methoxyphenyl)chromen-2-one (13), yield 39%, C 30 H 30 13, light yellow oil. PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.04, 2.10, 2.21 (12H, three s, four CH 3 C), 3.88 (3H, s, CH 3-4 ), (3H, m, H-5, CH 2-6 ), 5.05 (1H, d, J = 8.1, H-1 ), 5.15 (1H, dd, J = 3.3, J = 8.1, H-3 ), 5.51 (1H, d, J = 3.6, H-4 ), 5.62 (1H, dd, J = 8.1, J = 8.1, H-2 ), 6.26 (1H, s, H-3), 6.86 (1H, dd, J = 2.4, J = 8.7, H-6), 7.01 (1H, d, J = 2.4, H-8), 7.04 (2H, d, J = 8.4, H-3, H-5 ), 7.39 (2H, d, J = 8.4, H-2, H-6 ), 7.48 (1H, d, J = 8.7, H-5). 7-(2,3,4,6-Tetra--acetyl-β-D-galactopyranosyloxy)-8-methyl-4-(4-methoxyphenyl)chromen-2-one (14), yield 52%, C 31 H 32 13, mp C. IR spectrum (KBr, cm -1 ): 1758, 1698, 1604, 1514, 1370, 1248, PMR spectrum (400 MHz, CDCl 3, δ, ppm, J/Hz): 2.03, 2.05, 2.09, 2.21 (12H, four s, four CH 3 C), 2.32 (3H, s, CH 3-8), 3.89 (3H, s, CH 3-4 ), (3H, m, H-5, CH 2-6 ), 5.08 (1H, d, J = 8.1, H-1 ), 5.13 (1H, dd, J = 3.3, J = 8.1, H-3 ), 5.48 (1H, d, J = 3.6, H-4 ), 5.60 (1H, dd, J = 8.1, J = 8.1, H-2 ), 6.25 (1H, s, H-3), 6.93 (1H, d, J = 8.7, H-6), 7.03 (2H, d, J = 8.7, H-3, H-5 ), 7.35 (1H, d, J = 8.7, H-5), 7.38 (2H, d, J = 8.7, H-2, H-6 ). 7-(2,3,4-Tri--acetyl-β-D-xylopyranosyloxy)-4-phenylchromen-2-one (15), yield 41%, C 26 H 24 10, mp C. IR spectrum (KBr, cm -1 ): 1758, 1692, 1610, 1428, 1374, 1250, 1220, 1120, PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.11 (9H, s, CH 3 C-2, CH 3 C-3, CH 3 C-4 ), 3.59 (1H, dd, J = 12.0, J = 6.0, H-5 α), 4.22 (1H, dd, J = 12.0, J = 2.1, H-5 β), 5.04 (1H, m, H-4 ), (2H, m, H-2, H-3 ), 5.26 (1H, d, J = 7.2, H-1 ), 6.27 (1H, s, H-3), 6.86 (1H, dd, J = 2.1, J = 8.7, H-6), 7.04 (1H, d, J = 2.1, H-8), 7.41 (1H, d, J = 8.7, H-5), 7.44 (2H, m, H-2, H-6 ), 7.52 (3H, m, H-3, H-4, H-5 ). 7-(2,3,4-Tri--acetyl-α-D-arabinopyranosyloxy)-4-pheylchromen-2-one (16), yield 44%, C 26 H 24 10, mp C. IR spectrum (KBr, cm -1 ): 1744, 1696, 1612, 1374, 1248, 1236, 1218, 1090, PMR spectrum (300 MHz, CDCl 3, δ, ppm, J/Hz): 2.07, 2.09, 2.16 (9H, three s, four CH 3 C), 3.83 (1H, dd, J = 12.0, J = 2.1, H-5 α), 4.15 (1H, dd, J = 12.0, J = 6.0, H-5 β), 5.17 (1H, m, H-4 ), 5.20 (1H, d, J = 6.0, H-1 ), 5.36 (1H, m, H-3 ), 5.46 (1H, dd, J = 9.6, J = 10.2, H-2 ), 6.27 (1H, s, H-3), 6.89 (1H, dd, J = 2.4, J = 8.7, H-6), 7.06 (1H, d, J = 2.4, H-8), 7.41 (1H, d, J = 8.7, H-5), 7.44 (2H, m, H-2, H-6 ), 7.53 (3H, m, H-3, H-4, H-5 ). 7-Glycopyranosyloxy-4-arylchromen-2-ones A solution of peracetate 8-16 (4 mmol) in absolute MeH (20 ml) was treated with NaMe (20 mg). The reaction mixture was boiled for min (completion of reaction determined by TLC). The solid that precipitated on cooling (0 C) was filtered and washed with cold MeH. 7-(β-D-Glucopyranosyloxy)-4-phenylchromen-2-one (17), yield 87%, C 21 H 20 8, mp C. IR spectrum (KBr, cm -1 ): 3436, 1704, 1686, 1620, 1552, 1384, 1292, 1166, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): 3.18 (1H, m, H-4 ), 3.26 (2H, m, H-2, H-3 ), 3.44 (2H, m, H-5, H-6 α), 3.71 (1H, dd, J = 11.4, J = 2.4, H-6 β), 4.52 (1H, t, J = 5.7, H-6), 4.96 (1H, d, J = 7.5, H-1 ), 4.99 (1H, d, J = 4.2, H), 5.04 (1H, d, J = 3.9, H), 5.31 (1H, d, J = 4.2, H), 6.21 (1H, s, H-3), 6.97 (1H, dd, J = 2.4, J = 8.7, H-6), 7.12 (1H, d, J = 2.4, H-8), 7.37 (1H, d, J = 8.7, H-5), 7.50 (2H, m, H-2, H-6 ), 7.54 (3H, m, H-3, H-4, H-5 ). 7-(β-D-Glucopyranosyloxy)-8-methyl-4-phenylchromen-2-one (18), yield 94%, C 22 H 22 8, mp C. IR spectrum (KBr, cm -1 ): 3456, 1708, 1690, 1604, 1562, 1448, 1380, 1274, 1074, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): 2.33 (3H, s, CH 3-8), (4H, m, H-2, H-3, H-4, H-5 ), 3.45 (1H, dd, J = 11.4, J = 4.8, H-6 α), 3.65 (1H, dd, J = 11.4, J = 2.4, H-6 β), 4.35 (1H, t, J = 5.7, H-6), 4.89 (1H, d, J = 7.2, H-1 ), 5.01 (1H, d, J = 4.2, H), 5.12 (1H, d, J = 4.2, H), 5.29 (1H, d, J = 4.2, H), 6.19 (1H, s, H-3), 7.08 (1H, dd, J = 9.0, H-6), 7.23 (1H, d, J = 9.0, H-5), 7.49 (2H, m, H-2, H-6 ), 7.54 (3H, m, H-3, H-4, H-5 ). 7-(β-D-Glucopyranosyloxy)-4-(4-methoxyphenyl)-chromen-2-one (19), yield 86%, C 22 H 22 9, mp C. IR spectrum (KBr, cm -1 ): 3420, 2940, 1722, 1706, 1692, 1606, 1510, 1464, 1376, 1254, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): 3.17 (1H, m, H-4 ), 3.27 (2H, m, H-2, H-3 ), 3.40 (1H, m, H-5 ), 3.44 (1H, dd, J = 11.4, J = 4.8, H-6 α), 3.72 (1H, dd, J = 11.4, J = 2.4, H-6 β), 3.85 (3H, s, CH 3-4 ), 4.47 (1H, t, J = 5.7, H-6), 4.96 (1H, d, J = 7.5, H-1 ), 4.98 (1H, d, J = 4.2, H), 5.05 (1H, d, J = 3.9, H), 5.31 (1H, d, J = 4.2, H), 6.16 (1H, s, H-3), 6.97 (1H, dd, J = 2.4, J = 8.7, H-6), 7.08 (2H, d, J = 8.7, H-3, H-5 ), 7.10 (1H, d, J = 2.4, H-8), 7.44 (2H, d, J = 8.7, H-2, H-6 ), 7.46 (1H, d, J = 8.7, H-5). 666
5 7-(β-D-Galactopyranosyloxy)-4-phenylchromen-2-one (20), yield 82%, C 21 H 20 8, mp C. IR spectrum (KBr, cm -1 ): 3380, 1704, 1690, 1616, 1380, 1294, 1166, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): (6H, m, H-2, H-3, H-4, H-5, CH 2-6 ), 4.49 (1H, d, J = 4.5, H), 4.65 (1H, t, J = 5.7, H-6), 4.90 (1H, d, J = 4.5, H), 5.03 (1H, d, J = 7.5, H-1 ), 5.30 (1H, d, J = 4.2, H), 6.28 (1H, s, H-3), 7.00 (1H, dd, J = 2.1, J = 8.7, H-6), 7.16 (1H, d, J = 2.1, H-8), 7.37 (1H, d, J = 8.7, H-5), (5H, m, H-2, H-3, H-4, H-5, H-6 ). 7-(β-D-Galactopyranosyloxy)-8-methyl-4-phenylchromen-2-one (21), yield 89%, C 22 H 22 8, mp C. IR spectrum (KBr, cm -1 ): 3364, 1706, 1692, 1604, 1376, 1276, 1140, 1112, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): 2.33 (3H, s, CH 3-8), (6H, m, H-2, H-3, H-4, H-5, CH 2-6 ), 4.40 (1H, d, J = 4.5, H), 4.61 (1H, t, J = 5.7, H-6), 4.68 (1H, d, J = 4.5, H), 4.82 (1H, d, J = 7.5, H-1 ), 5.15 (1H, d, J = 4.2, H), 6.18 (1H, s, H-3), 7.08 (1H, dd, J = 9.0, H-6), 7.22 (1H, d, J = 9.0, H-5), 7.49 (2H, m, H-2, H-6 ), 7.54 (3H, m, H-3, H-4, H-5 ). 7-(β-D-Galactopyranosyloxy)-4-(4-methoxyphenyl)chromen-2-one (22), yield 91%, C 22 H 22 9, mp C. IR spectrum (KBr, cm -1 ): 3396, 2912, 1706, 1690, 1608, 1548, 1510, 1380, 1250, 1212, 1088, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): (6H, m, H-2, H-3, H-4, H-5, CH 2-6 ), 3.85 (3H, s, CH 3-4 ), 4.45 (1H, d, J = 4.5, H), 4.58 (1H, t, J = 5.7, H-6), 4.79 (1H, d, J = 4.5, H), 4.93 (1H, d, J = 7.5, H-1 ), 5.16 (1H, d, J = 4.2, H), 6.15 (1H, s, H-3), 6.96 (1H, dd, J = 2.1, J = 8.7, H-6), 7.07 (2H, d, J = 8.7, H-3, H-5 ), 7.10 (1H, d, J = 2.1, H-8), 7.45 (3H, d, J = 8.7, H-5, H-2, H-6 ). 7-(β-D-Galactopyranosyloxy)-8-methyl-4-(4-methoxyphenyl)chromen-2-one (23), yield 93%, C 23 H 24 9, mp C. IR spectrum (KBr, cm -1 ): 3420, 1704, 1690, 1608, 1510, 1372, 1284, 1254, PMR spectrum (300 MHz, DMS-d 6, δ, ppm, J/Hz): 2.33 (3H, s, CH 3-8), (6H, m, H-2, H-3, H-4, H-5, CH 2-6 ), 3.85 (3H, s, CH 3-4 ), 4.45 (1H, d, J = 4.5, H), 4.53 (1H, t, J = 5.7, H-6), 4.75 (1H, d, J = 4.5, H), 4.83 (1H, d, J = 7.8, H-1 ), 5.18 (1H, d, J = 4.2, H), 6.14 (1H, s, H-3), 7.07 (3H, d, J = 8.7, H-6, H-3, H-5 ), 7.30 (1H, d, J = 8.7, H-5), 7.44 (2H, d, J = 8.7, H-2, H-6 ). 7-(β-D-Xylopyranosyloxy)-4-phenylchromen-2-one (24), yield 87%, C 20 H 18 7, mp C. IR spectrum (KBr, cm -1 ): 3452, 1712, 1612, 1380, 1278, 1160, 1112, PMR spectrum (400 MHz, DMS-d 6, δ, ppm, J/Hz): (4H, m, H-2, H-3, H-4, H-5 a), 3.76 (1H, m, H-5 e), 4.95 (1H, d, J = 6.9, H-1 ), 5.03 (1H, d, J = 4.5, H), 5.08 (1H, d, J = 3.9, H), 5.34 (1H, d, J = 4.8, H), 6.28 (1H, s, H-3), 7.00 (1H, dd, J = 2.1, J = 8.7, H-6), 7.16 (1H, d, J = 2.1, H-8), 7.37 (1H, d, J = 8.7, H-5), (5H, m, H-2, H-3, H-4, H-5, H-6 ). 7-(α-D-Arabinopyranosyloxy)-4-phenylchromen-2-one (25), yield 82%, C 20 H 18 7, mp C. IR spectrum (KBr, cm -1 ): 3408, 1712, 1610, 1376, 1208, 1152, PMR spectrum (400 MHz, DMS-d 6, δ, ppm, J/Hz): 3.48 (1H, m, H-4 ), (4H, H-2, H-3, CH 2-5 ), 4.59 (1H, d, J = 4.2, H), 4.77 (1H, d, J = 5.4, H), 4.98 (1H, d, J = 6.9, H-1 ), 5.22 (1H, d, J = 4.8, H), 6.25 (1H, s, H-3), 7.01 (1H, dd, J = 2.1, J = 8.7, H-6), 7.15 (1H, d, J = 2.1, H-8), 7.38 (1H, d, J = 8.7, H-5), (5H, m, H-2, H-3, H-4, H-5, H-6 ). ACKNWLEDGMENT We thank A "Eksimed" (Kiev, Ukraine) for assistance with the work. REFERENCES 1. R. D. H. Murray, The Naturally ccurring Coumarins, Springer, Vienna-New York (2002). 2. M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Khim. Prir. Soedin., 47 (2003). 3. A. Ulubelen, R. R. Kerr, and T. J. Mabry, Phytochemistry, 21, 1145 (1982). 4. D. Kumar and D. K. Mukharya, Acta Cienc. Indica, Chem., 16C(4), 411 (1990); Chem. Abstr., 116, w (1992). 667
6 5. R. Mata, M. del R. Camacho, S. Mendoza, and M. del C. Cruz, Phytochemistry, 31, 3199 (1992). 6. L. L. Woods and J. Sapp, J. rg. Chem., 27, 3703 (1962). 7. M. M. Garazd, Ya. L. Garazd, A. S. gorodniichuk, and V. P. Khilya, Khim. Prir. Soedin., 428 (2002). 8. V. G. Pivovarenko, V. P. Khilya, V. N. Kovalev, and S. A. Vasil ev, Khim. Prir. Soedin., 511 (1988). 9. V. G. Pivovarenko, V. P. Khilya, V. N. Kovalev, and S. A. Vasil ev, Khim. Prir. Soedin., 519 (1988). 10. M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Khim. Prir. Soedin., 7 (2004). 11. J. F. Stoddart, Stereochemistry of Carbohydrates, Interscience, New York (1971). 12. C. E. Redemann and C. Niemann, rganic Syntheses, Vol. 22, John Wiley & Sons, New York (1942), p N. K. Kochetkov, Methods of Carbohydrate Chemistry [in Russian], Mir, Moscow (1967). 668
SYNTHESIS OF AMINO ACID DERIVATIVES OF HYDRAZONES AND OXIMES OF SPIRODIHYDRO- PYRANOCHROMEN-2-ONES
Chemistry of eterocyclic Compounds, Vol. 44, o. 2, 2008 SYTESIS F AMI ACID DEIVATIVES F YDAZES AD XIMES F SPIDIYD- PYACME-2-ES M. V. Veselovska, M. M. Garazd,. S. gorodniychuk, Ya. L. Garazd 2, and V.
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationMaksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov
1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv
More informationSupporting Information. Table of Contents. 1. General Notes Experimental Details 3-12
Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents
More informationDimethyl Sulphoxide-Acetic Anhydride: An Excellent Source of Formaldehyde and Thiomethanol
Asian Journal of Chemistry Vol. 20, No. 2 (2008), 929-933 Dimethyl Sulphoxide-Acetic Anhydride: An Excellent Source of Formaldehyde and Thiomethanol KHALIDA TASNEEM* and KHALIQUZ ZAMAN KHAN Department
More informationCHAPTER 8 ISOLATION AND CHARACTERIZATION OF PHYTOCONSTITUENTS BY COLUMN CHROMATOGRAPHY
146 CHAPTER 8 ISLATIN AND CHARACTERIZATIN F PHYTCNSTITUENTS BY CLUMN CHRMATGRAPHY 8.1 INTRDUCTIN Column chromatography is an isolation technique in which the phytoconstituents are being eluted by adsorption.
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationSupplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supplementary Information Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated
More information*Corresponding author. Tel.: , ; fax: ; Materials and Method 2. Preparation of GO nanosheets 3
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3h)-one catalyzed by Graphene Oxide
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationSupporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones
Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università
More informationSupporting Information
S1 Microwave-Assisted Synthesis of Isonitriles: A General Simple Methodology Andrea Porcheddu,* Giampaolo Giacomelli, and Margherita Salaris Dipartimento di Chimica, Università degli Studi di Sassari,
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More information2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide
217 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide O O Cl NH 3 NH 2 C 9 H 7 ClO (166.6) (17.) C 9 H 9 NO (147.2) Classification Reaction types and substance classes reaction of
More informationScalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis
Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis Fei Yu, Matthew S. McConnell, and Hien M. Nguyen* Department of Chemistry, University of Iowa, Iowa
More informationN-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
More informationA "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media
A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media Styliani Voutsadaki, George K. Tsikalas, Emmanuel Klontzas, George E. Froudakis, and Haralambos E.
More informationCopper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Copper-Catalyzed xidative Cyclization of Carboxylic Acids Supplementary material (51 pages) Shyam Sathyamoorthi and J. Du Bois * Department of Chemistry Stanford University Stanford, CA 94305-5080 General.
More informationISATIN (PER-O-ACETYL- -D- GALACTOPYRANOSYL)THIOSEMICARBAZONES
ISATIN (PER--ACETYL- -D- GALACTPYRANSYL)THISEMICARBAZNES Nguyen Dinh Thanh*, Nguyen Thi Kim Giang Faculty of Chemistry, College of Science, Vietnam National University (Hanoi), 19 Le Thanh Tong, Hanoi
More informationPoly(4-vinylimidazolium)s: A Highly Recyclable Organocatalyst Precursor for. Benzoin Condensation Reaction
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supporting Information Poly(4-vinylimidazolium)s: A Highly Recyclable rganocatalyst Precursor
More informationSupporting Information
Supporting Information Nano CuFe 2 O 4 as a Magnetically Separable and Reusable Catalyst for the Synthesis of Diaryl / Aryl Alkyl Sulfides via Cross-Coupling Process under Ligand Free Conditions Kokkirala
More informationFacile Synthesis of Flavonoid 7-O-Glycosides
Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
More informationElectronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012
Supporting Information. Experimental Section: Summary scheme H 8 H H H 9 a H C 3 1 C 3 A H H b c C 3 2 3 C 3 H H d e C 3 4 5 C 3 H f g C 2 6 7 C 2 H a C 3 B H c C 3 General experimental details: All solvents
More informationChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationSupplementary Information
Facile Preparation of Fluorovinylene Aryl Ether Telechelic Polymers with Dual Functionality for Thermal Chain Extension and Tandem Crosslinking Scott T. Iacono, Stephen M. Budy, Dirk Ewald, and Dennis
More informationSupporting Information
Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationhydroxyanthraquinones related to proisocrinins
Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,
More informationSupporting Information File 1 For. A novel family of (1-aminoalkyl)(trifluoromethyl)- and -
Supporting Information File 1 For A novel family of (1-aminoalkyl)(trifluoromethyl)- and - (difluoromethyl)phosphinic acids analogues of α-amino acids Natalia V. Pavlenko 1, Tatiana I. Oos 1, Yurii L.
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014 Electronic Supporting Information
More informationA Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationSupporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using
More informationRational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+
Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei
More informationSupporting Information
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
More informationRegioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System Doris Lee and Mark S. Taylor* Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St.
More informationSupporting Information
Supporting Information One Pot Synthesis of 1,3- Bis(phosphinomethyl)arene PCP/PNP Pincer Ligands and Their Nickel Complexes Wei-Chun Shih and Oleg V. Ozerov* Department of Chemistry, Texas A&M University,
More informationAppendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
More informationIndium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationSupporting Information
Supporting Information Electrochemical generation of silver scetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids Koichi Mitsudo,*
More informationElectronic Supplementary Information
Electronic Supplementary Information A new chemo-enzymatic route to chiral 2-hydroxy-4-phenylbutyrates by combining lactonase-mediated resolution with hydrogenation over Pd/C Bing Chen, a Hai-Feng Yin,
More informationSynthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond
More informationSelective Synthesis of 1,2- cis- α- Glycosides in the Absence of Directing Groups. Application to Iterative Oligosaccharide Synthesis.
Selective Synthesis of 1,2- cis- α- Glycosides in the Absence of Directing Groups. Application to Iterative ligosaccharide Synthesis. An- Hsiang Adam Chu, Son Hong Nguyen, Jordan A Sisel, Andrei Minciunescu,
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationChemical synthesis (see also reaction scheme, bold underlined numbers in this text refer to the bold underlined numbers in the scheme)
Supplementary Note This section contains a detailed description of the chemical procedures and the characterization of products. The text is followed by a reaction scheme explaining the synthetic strategies
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationpyrazoles/isoxazoles library using ketene dithioacetals
Water mediated construction of trisubstituted pyrazoles/isoxazoles library using ketene dithioacetals Mahesh M. Savant, Akshay M. Pansuriya, Chirag V. Bhuva, Naval Kapuriya, Anil S. Patel, Vipul B. Audichya,
More information4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester
NP 4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester NaEt C 10 H 18 4 Na C 2 H 6 C 8 H 12 3 (202.2) (23.0) (46.1) (156.2) Classification Reaction types and substance
More informationSupporting Information. for. Angew. Chem. Int. Ed Wiley-VCH 2004
Supporting Information for Angew. Chem. Int. Ed. 200460176 Wiley-VCH 2004 69451 Weinheim, Germany Iterative ne-pot ligosaccharide Synthesis Xuefei Huang, a * Lijun Huang a, Haishen Wang b, and Xin-Shan
More informationSupporting Information
Supporting Information for Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C Abhishek Santra, Tamashree Ghosh and Anup Kumar Misra * Address: Bose
More informationSupplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and
More informationo-aminomethylderivatives of phenols. Part 3. Mechanistic investigation of a Mannich reaction of phenols with N-methylenealkylamines
o-aminomethylderivatives of phenols. Part 3. Mechanistic investigation of a Mannich reaction of phenols with N-methylenealkylamines Krzysztof Bujnowski, Agnieszka Adamczyk-Woźniak, and Ludwik Synoradzki*
More informationSYNTHESIS OF A 3-THIOMANNOSIDE
Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,
More informationSupporting Information
Supporting Information A Combined Effect of the Picoloyl Protecting Group and Triflic Acid in Sialylation Samira Escopy, Scott A. Geringer and Cristina De Meo * Department of Chemistry Southern Illinois
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten
More informationSupporting Information For:
Supporting Information For: Highly Fluorinated Ir(III)- 2,2 :6,2 -Terpyridine -Phenylpyridine-X Complexes via Selective C-F Activation: Robust Photocatalysts for Solar Fuel Generation and Photoredox Catalysis
More informationFast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.
Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,
More informationSupporting Information
Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in
More information5.37 Introduction to Organic Synthesis Laboratory
MIT pencourseware http://ocw.mit.edu 5.37 Introduction to rganic Synthesis Laboratory Spring 2009 For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms. URIECA
More informationDie Belichtungsapparatur ist in der Saalausleihe erhältlich
rganisches Praktikum CP II Wintersemester 2009/10 Versuch 27 Photooxidation von 1,5-Dihydroxynaphthalin zu Juglon, Betreuer: Literatur: Robert Lechner NP Versuch 7001 (www.oc-praktikum.de) Chemikalien:
More informationSupplementary Information. Low volume shrinkage polymers by photo Polymerization of 1,1- Bis(ethoxycarbonyl)-2-vinylcyclopropanes
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information Low volume shrinkage polymers by photo Polymerization of 1,1-
More informationSupporting Information:
Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 Supporting Information Palladium-Catalyzed Construction of Spirooxindoles by Arylative Cyclization of 3-( -Disubstituted)allylidene-2-Oxindoles
More informationSynthesis of borinic acids and borinate adducts using diisopropylaminoborane
Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,
More informationSupporting Information
ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei
More informationElectronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012
Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,
More informationSupplementary Materials. Table of contents
Supplementary Materials Microwave- Assisted Multicomponent Ecofriendly Synthesis of 3-Bihetaryl-2-oxindole Derivatives Grafted with Phenothiazine Moiety A. S. Al-Bogami 1 and A. S. El-Ahl 1,2 * 1 Chemistry
More informationSynthesis and structural analysis of anilides of. glucuronic acid and orientation of groups on
Synthesis and structural analysis of anilides of glucuronic acid Tosin, Brien et al. S1 Synthesis and structural analysis of anilides of glucuronic acid and orientation of groups on carbohydrate scaffolding.
More informationRegioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable
1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was
More informationSupporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
More informationStraightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol
S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien
More informationSupporting Information
Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
More informationSupporting Information. Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins
Supporting Information Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins Christiane Schultze and Bernd Schmidt for Beilstein J. Org. Chem. 2018, 14, 2991 2998. doi:10.3762/bjoc.14.278
More informationSupporting Information
Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry
More informationFigure S1 - Enzymatic titration of HNE and GS-HNE.
Figure S1 - Enzymatic titration of HNE and GS-HNE. Solutions of HNE and GS-HNE were titrated through their reduction to the corresponding alchools catalyzed by AR, monitoring the decrease in absorbance
More informationAn unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP)
This journal is The Royal Society of Chemistry 213 Supplementary Information for An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP) Lei Shi, Ping Hu, Yanliang Ren and
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Lei Liu, ab Yijie Xia, b Jie Zhang* b a) China Center for Modernization
More informationTriazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3
Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,
More informationSUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
More informationMetal-free general procedure for oxidation of secondary amines to nitrones
S1 Supporting information Metal-free general procedure for oxidation of secondary amines to nitrones Carolina Gella, Èric Ferrer, Ramon Alibés, Félix Busqué,* Pedro de March, Marta Figueredo,* and Josep
More informationDepartment of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures
Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher
More informationSupporting Information
1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche
More informationSupporting Information
Supporting Information for Engineering of indole-based tethered biheterocyclic alkaloid meridianin into -carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
More informationSupporting Information (SI)
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting Information (SI) Interactions, Morphology and Thermal Stability of Graphene-xide
More informationChapter IV. Secondary Ammonium Salts
Chapter IV Secondary Ammonium Salts IV.1. Introduction Several secondary ammonium salts with hexafluorophosphate counterions were synthesized. To study the complexation behavior of these salts in solution
More informationCoupling of 6 with 8a to give 4,6-Di-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-Dglucopyranosyl-(1 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose.
General Experimental Procedures. NMR experiments were conducted on a Varian Unity/Inova 400-MHz Fourier Transform NMR Spectrometer. Chemical shifts are downfield from tetramethylsilane in CDCl 3 unless
More informationBrønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
More informationSupporting Information for Polybenzimidazolium Salts: A New Class of. Anion-Conducting Polymer
Supporting Information for Polybenzimidazolium Salts: A ew Class of Anion-Conducting Polymer Owen D. Thomas, Kristen J. W. Y. Soo, Timothy J. Peckham, Mahesh P. Kulkarni and Steven Holdcroft* Department
More informationSerendipitous synthesis of 1,4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl]aniline
erendipitous synthesis of 1,4-benzothiazin derivatives using 2-[(2-aminophenyl)disulfanyl]aniline Mohammad Reza Islami a *, Fouziyeh Mollazehi a, Alireza Badiei b, and assan heibani a a Department of Chemistry,
More informationSYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES
SYNTHESIS AND ANTIBACTERIAL EVALUATION OF NOVEL 3,6- DISUBSTITUTED COUMARIN DERIVATIVES 1 Ravibabu Velpula, 1 Ramesh Gondru, 2 Yashodhara Velivela and 1 Rajitha Bavantula* 1 Department of Chemistry, National
More informationSupporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via
Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via Mitsunobu reactions. Guijun Wang,*Jean Rene Ella-Menye, Michael St. Martin, Hao Yang, Kristopher
More informationCarbonylative Coupling of Allylic Acetates with. Arylboronic Acids
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Carbonylative Coupling of Allylic Acetates with Arylboronic Acids Wei Ma, a Ting Yu, Dong Xue,*
More informationSupporting Information for: Tuning the Binding Properties of a New Heteroditopic Salt Receptor Through Embedding in a Polymeric System
Supporting Information for: Tuning the Binding Properties of a ew Heteroditopic Salt Receptor Through Embedding in a Polymeric System Jan Romanski* and Piotr Piątek* Department of Chemistry, University
More informationPhotolysis for Vitamin D Formation. Supporting Information
S1 Synthesis of 1α-Hydroxyvitamin D 5 Using a Modified Two Wavelength Photolysis for Vitamin D Formation Supporting Information Robert M. Moriarty and Dragos Albinescu Spectra 1. 13 C: 3β-Acetoxy-stigmasta-5,7-diene
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationA New, Powerful Glycosylation Method: Activation of Thioglycosides with Dimethyl Disulfide-Triflic Anhydride. János Tatai and Péter Fügedi*
A New, Powerful Glycosylation Method: Activation of Thioglycosides with Dimethyl Disulfide-Triflic Anhydride János Tatai and Péter Fügedi* Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri
More information