Supporting Information: Regioselective esterification of vicinal diols on monosaccharide derivatives via

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1 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 Williams Table of contents s1 Synthesis of compounds 20, 22, 24, 25, 27, 35, 36, S2 References...S11 Figure 1. 1 H and 13 C NMR spectra of compound S12 Figure 2. 1 H spectra of compound 21 and hydrolysis product of S13 Figure 3. 1 H and 13 C NMR spectra of compound S15 Figure 4. 1 H and 13 C NMR spectra of compound S16 Figure 5. 1 H and 13 C NMR spectra of compound S17 Figure 6. 1 H and 13 C NMR spectra of acetylated compound S18 Figure 7. 1 H and 13 C NMR spectra of compound S19 Figure 8. 1 H and 13 C NMR spectra of compound S20 Figure 9. 1 H and 13 C NMR spectra of compound S21 Figure 10. Crude 1 H NMR spectra of compound 27 (BzH)......S22 Figure 11. Crude 1 H NMR spectra of compound 27 (BzSH) S23 Figure H and 13 C NMR spectra of compound S24 Figure H and 13 C NMR spectra of compound S25 Figure H and 13 C NMR spectra of compound S26 S1

2 Figure H and 13 C NMR spectra of compound S27 Figure H and 13 C NMR spectra of compound S28 Figure H and 13 C NMR spectra of compound S29 S2

3 Experimental section: The general reagents used for all Mitsunobu reactions: 1 equivalent of sugar derivatives, 2 equivalents of TPP, DEAD, and BzH, and THF as solvent. The addition of TPP and DEAD is done at 0 C, after 30 minutes, BzH is added, and then the reaction is raised to room temperature, or heated to 50 to 70 C. After the reaction is worked up, depending on the structure of the products, two or three column purifications using flash chromatography may be necessary, especially for mannose diol derivatives. In most reactions, the byproduct of DEAD seems to interfere with separation, careful selection of solvent systems is important for the purification. New reagents such as DMEAD that produces more water soluble byproduct can be used to help with the isolation. This reagent gives almost the same results as using DEAD. The best results are obtained with benzoic acid, when the same Mitsunobu reactions were carried out using 4-nitrobenzoic acid instead of benzoic acid, almost no esterification reactions were observed. These include using diols 15, 23, 26, and 34, at similar conditions as using benzoic acid. The 4-nitrobenzoic acid is a stronger acid therefore the 4-nitrobenzoate is less nucleophilic (less basic as well) comparing to benzoate. This lower reactivity of the anion towards the intermediate 3 or 4 is perhaps responsible for the low reactivity of the overall reaction. The formation of the triphenylphosphonium (N2-CP + 3) ion is hindered and as a result, hindering the reaction to go further. The preparation and characterization of compounds 20, 22, 24, 25, 27, 35, 36, are provided on pages S4-S11. Compounds 24, 25, 27, 35, 36, are known compounds that have been reported before, the references to these compounds are provided on page S11. S3

4 Preparation of compound 20. P 3, DEAD BzH/THF, 0 o C-RT H Bz Compound 19 (0.430 g, 1.82 mmol) was dissolved in anhydrous THF (0 ml) at 0 C. Triphenylphosphine (0.955 g, 3.64 mmol) and DEAD (40% in toluene, 1.66 ml, 3.64 mmol) were added to the solution, which was stirred for 30 min. at room temperature. Benzoic acid (0.444 g, 3.64 mmol) was added to the solution and the reaction was stirred at room temperature for 20 h. The solution was cooled to 0 C and the reaction was quenched with saturated NaHC 3. After evaporating the THF, CH 2 Cl 2 was added and the organic phase was washed with H 2 two to three times. After drying on Na 2 S 4, filtration and concentration, the crude mixture was purified on Si 2 gel using a solvent system of hexane:ch 2 Cl 2 :THF 30:1:1. The pure product (0.430 g, 1.26 mmol) was isolated as a white solid. Yield: 69%. 1 H NMR (CDCl 3, 400MHz) δ 8.11 (m, 2H), (m, 8H), 5.65 (s, 1H), 5.37 (m, 1H), 4.34 (dd, 1H, J = 10.6, 5.1 Hz), 4.18 (d, 1H, J = 1 Hz), 6 (m, 1H), 3.81 (m, 2H), 3.47 (dt, 1H, J = 9.5, 5.1 Hz), 2.47 (m, 1H), 2 (m, 1H). 13 C NMR (CDCl 3, 100MHz) δ 165.8, 137.4, 133.2, 130.2, 129.8, 129.1, 128.4, 128.3, 126.1, 101.9, 74.6, 73.8, 69.8, 69.7, 6, HRMS: Calcd for C 20 H 21 5 [M+H] , found Preparation of compound 22. Bn 21 H P 3, DEAD C 2 H/THF, 0-RT Bn 22 Bz S4

5 3-Benzyl-4,6--benzylidene-1,5-anhydro-D-glucitol 21 (106 mg, mmol) was dissolved in anhydrous THF (0 ml). Triphenylphosphine (162 mg, mmol) and DEAD (40%, wt in toluene, ml, mmol) were added at 0 C. After stirring at room temperature for 2 h benzoic acid (7 mg, mmol) was added and the solution was stirred for another 22 h. The THF was evaporated, CH 2 Cl 2 was added and the organic phase was washed with H 2 two to three times. After drying on Na 2 S 4, filtration and concentration, the crude mixture was purified on Si 2 gel using a solvent system of hexane/ch 2 Cl 2/ THF 30:1:1. The pure product was isolated as white solid (124 mg, mmol). Yield: 90%. 1 H NMR (CDCl 3, 400MHz) δ 7.97 (d, 2H, J = 7.1 Hz), (m, 13H), 5.63 (s, 1H), 5.27 (ddd, 1H, J = 10.6, 9.2, 5.9 Hz), 4.90 (d, 1H, J = 1 Hz), 4.80 (d, 1H, J = 1 Hz), 4.37 (dd, 1H, J = 10.6, 4.9 Hz), 4.25 (dd, 1H, J = 1, 5.9 Hz), 3.93 (t, 1H, J = 9.2 Hz), 3.79 (m, 2H), 3.46 (dt, 1H, J = 9.5, 4.9 Hz), 3.39 (dd~t, 1H, J = 1, 10.6 Hz). 13 C NMR (CDCl 3, 100MHz) δ 16, 13, 137.3, 133.2, 129.7, 129.4, 128.9, 128.3, 128.2, 128.1, 127.9, 12, 125.9, 101.2, 81.9, 78.8, 74.2, 71.4, 68.6, HRMS: Calcd for C 27 H 27 6 [M+H] , found Preparation of compound In reference 1, compound 24 was prepared by direct benzoylation reaction using BzCl and pyridine at 0 C for 24 h in 27.6% yield, together with 42.3% 3-Bz, 16.6% dibenzoate. H H P 3, DEAD BzH/THF, 0 o C-RT H Bz ,6--Benzylidene-1-deoxy-D-glucopyranoside 23 (0 g, 3.96 mmol) was dissolved in anhydrous THF (10.0 ml) and cooled to 0 C. Triphenylphosphine (2.10 g, 1 mmol) and S5

6 DEAD (40% in toluene; 4.40 ml, 9.66 mmol) were then sequentially added to the mixture. The solution was stirred at room temperature for 15 min, and benzoic acid (0 g, 8.19 mmol) was added to the mixture. After stirring at room temperature for 12 h, the reaction was cooled to 0 C and quenched with saturated NaHC 3 solution. The THF was evaporated, and the crude mixture was diluted with CH 2 Cl 2 and washed with H 2 twice then dried on Na 2 S 4. After filtration and concentration, the crude mixture was purified on Si 2 gel with a solvent gradient of pure hexane to hexane:acetone 15:1. The pure product (1.33 g, 3.73 mmol) was isolated as a white solid. Yield: 94%. 1 H NMR (CDCl 3, 400MHz) δ 5 (d, 2H, J = 7.1 Hz), (m, 8H), 7 (s, 1H), 5.19 (ddd, 1H, J = 10.6, 9.2, 5.9 Hz), 4.36 (dd, 1H, J = 10.3, Hz), 4.26 (dd, 1H, J = 1, 5.9 Hz), 8 (t, 1H, J = 9.2 Hz), 3.75 (t, 1H, J = 10.3 Hz), 3.61 (dd~t, 1H, J = 9.5, 9.2 Hz), 3.45 (m, 2H). 13 C NMR (CDCl 3, 100MHz) δ 16, 136.9, 133.3, 129.7, 129.3, 129.2, 128.4, 128.3, 126.3, 101.8, 81.1, 72.6, 72.1, 7, 6, Preparation of 2-benzoyl-4,6--benzylidene-methyl-α-D-glucopyranoside H 18 P 3, DEAD C 2 H/THF, 0-60 o C H Me H 25 Bz Me 4,6--benzylidene-methyl-α-D-glucopyranoside 18 (103 mg, mmol) was dissolved in anhydrous THF (0 ml). Triphenylphosphine (287 mg, 9 mmol) and DEAD (97%, ml, 9 mmol) were added at 0 C. After stirring at room temperature for 1 h benzoic acid (34.2 mg, mmol) was added and the solution was stirred for another 20 h. The temperature was then raised to 60 C and the reaction was stirred for an additional 20 h. The THF was evaporated, CH 2 Cl 2 was added and the organic phase was washed with H 2 two to three times. S6

7 After drying on Na 2 S 4, filtration and concentration, the crude mixture was purified on Si 2 gel using a solvent system of hexane:ch 2 Cl 2 :THF = 30:1:1. The pure product was isolated as colorless oil (113 mg, mmol). Yield: 80%. 1 H NMR (CDCl 3, 400MHz) δ 8.10 (d, 2H, J = 7.7 Hz), (m, 8H), 8 (s, 1H), 8 (d, 1H, J = 3.7Hz), 5 (dd, 1H, J = 9.5, 3.7 Hz), 4.35 (m, 2H), 3.92 (dt, 1H, J = 9.9, 4.8 Hz), 3.81 (t, 1H, J = 10.3 Hz), 3.65 (t, 1H, J = 9.4 Hz), 3.40 (s, 3H). 13 C NMR (CDCl 3, 100MHz) δ 166.2, 136.9, 133.4, 129.9, 129.4, 129.3, 128.4, , 126.3, 10, 97.7, 81.4, 7, 68.9, 68.8, 6, 5. Preparation of compound PMP P 3, DEAD PMP H H CSH/THF, 0-60 o C H Me Bz Me Preparation of compound 27 using thiobenzoic acid: Triethylamine (0.134ml, 0.96mmol), thiobenzoic acid (0.074ml, 0.64mmol) and THF (1mL) were mixed first, to this mixture compound 26 (100mg, 0.32mmol) dissolved in 1mL of THF was added. The reaction mixture was cooled in ice bath, then triphenylphosphine (0.168g, 0.64mmol) was added to the mixture, it was left stirring for about 5 minutes, diethyl azodicarboxylate (DEAD 97%) (0.1ml, 0.64mmol) was added to the mixture, it was allowed standing for another 5-10 minutes, the reaction mixture was then heated in oil bath to 60 C for two days. After which time the 1H NMR spectrum indicated roughly 40% conversion and 60% starting materials. The crude mixture was dried to remove solvent and then purified using flash chromatograph on silica gel. The solvent system is Hexane: Dichloromethane: THF = 30:1:1, the purified product 27 was obtained as a white solid, yield, 41mg, 30%. 1 H NMR (CDCl 3, 400MHz) δ 9 (m, pseudo doublet, 2H), 8 (t, 1H, J = S7

8 7.3Hz), (m, 4H), 6.90 (d, 2H, J = 8.8Hz), 3 (s, 1H), 7 (d, 1H, J = Hz), 3 (dd, 1H, J = 9.5, Hz), 4.32 (m, 2H), 3.89 (td, 1H, J = 9.9, 4.8 Hz), 3.80 (s, 3H), 3.78 (t, 1H, J = 10.3 Hz), 3.61 (t, 1H, J = 9.4 Hz), 3.39 (s, 3H). 13 C NMR (CDCl 3, 100MHz) δ 166.2, 160.2, 133.3, 129.9, 129.4, 128.4, 127.6, 113.7, 10, 97.7, 7, 68.83, 68.76, 6, 5, The compound 27 was also prepared using the same starting material 26 and benzoic acid as the acylating agent, after 2 days, 1 H NMR indicated >90% conversion, the isolated yield after chromatography is 75%. The NMR spectra of compound 27 and the crude reaction mixture of the two reactions are shown on page S22-S23. Preparation of compound H P 3, DMEAD BzH/THF, 0 o C-60 o C H H Bz Compound 34 (0 g, 3.96 mmol), was dissolved in anhydrous THF (0 ml) at 0 C. Triphenylphosphine (2.10 g, 0 mmol) and DMEAD (1.84 g, 7.86 mmol) were added and the solution was stirred at room temperature for 30 min. Benzoic acid (0.976 g, 7.99 mmol) was added and the reaction was stirred a room temperature for 10 min. then at 60 C for 36 h. THF was evaporated under vacuum and the crude mixture was dissolved in CH 2 Cl 2. The organic phase was washed with saturated NaHC 3 and H 2 thrice, then dried on Na 2 S 4. After filtration and concentration, the crude mixture was purified on Si 2 gel using a gradient of pure hexane to hexane:acetone 6:1, then recrystallized using a mixture of hexane and ethyl acetate. The pure S8

9 product (1.20 g, 3.37mmol) was obtained as a white solid. Yield: 85%. 1 H NMR (CDCl 3, 400MHz) δ 5 (m, 2H), (m, 8H), 5.60 (s, 1H), 5.44 (ddd~td, 1H, J = 10.1, 5.1 Hz), 4.34 (m, 2H), 4.30 (dd, 1H, J = 1, 5.1), 7 (dd, 1H, J = 1, 1.6 Hz), 3.91 (dd, 1H, J = 9.7, 3.7 Hz), 3.48 (m, 1H), 3.40 (dd~t, 1H, J = 1, 10.6 Hz). 13 C NMR (CDCl 3, 100MHz) δ 166.3, 137.3, 133.3, 129.8, 129.3, 128.4, 128.3, 126.3, 10, 76.2, 72.2, 70.4, 70.3, 69.5, 6. General procedure for compound H 34 H BzCl, Py DCM, 0 C Bz 36 H In a dry small round bottom flask, compound 36 dissolved in DCM was the reaction mixture was protected from moisture using a CaCl 2 drying tube. After the mixture was cooled to 0 C in an ice bath, pyridine and benzoyl chloride were added to the flask and the reaction mixture was left stirring for 2 hours, at which time 1 H NMR indicated >95% conversion, the 3-ester is about 85-95% and the dieseter is about 5-10%. The reaction mixture was quenched with ice-water, organic phase was separated and dried over Na 2 S 4. The crude product was purified on silica gel using hexane:etac 5:1 solvent system. The crude product yield after working up is 93%. The pure compound 36 was obtained as a white crystalline powder in 65% yield after column purification. A small amount of diester and starting material were also recovered after the chromatography. 1 H NMR (CDCl 3, 400MHz) δ 2 (d, 2H, J = 7.3 Hz), (m, 8H), 2 (s, 1H), 4 (dd, 1H, J = 9.9, 3.7 Hz), 0 (d, 1H, J = 3.7 Hz), H (ddd~td, J = 10.3, 9.9, ), 4.29 (dd, 1H, J = 1, Hz ), 4.20 (dd, 1H, J = 11.4, Hz), 3 (dd, 1H, J = 1, Hz), 3.47 (bs, 1H), S9

10 3.37 (dd~t, 1H, J = 10.3, 11.4 Hz). 13 C NMR (CDCl 3, 100MHz) δ 166.8, 137.6, 133.4, 129.8, 129.5, 128.8, 128.4, 12, 12, 100.6, 76.8, 74.1, 69.9, 69.7, 69.4, Preparation of by direct benzoylation reaction H 38 BzCl, Py DCM, 0 C-rt Bz H Me + + H Bz H Bz Bz Me Me Me Similar method as the preparation of 36 was used here. Bezoyl chloride 1.1 equivalent, the reaction was run at 0 C first and then room temperature for 14 hrs. The compounds were isolated by flash chromatography using hexane/dcm/thf, 15:1:1. The diester 41 was isolated first, yield 17%. 1 H NMR (CDCl 3, 400MHz) (m, 4H), (m, 4H), (m, 7H), 5.80 (m, 2H), 8 (s, 1H), 5.29 (d, 1H, J = 2.2 Hz), 4.66 (m, 1H), 4.36 (dd, 1H, J = 1, Hz), 4.14 (dd, 1H, J = 1, Hz), 3.91 (m, pseudo s, 1H), 3.47 (s, 3H). 13 C NMR (CDCl 3, 100MHz) δ 166.2, 165.9, 13, , , , , 129.5, 129.4, 128.9, 128.3, 128.1, 126.1, 100.6, 98.1, 74.2, 69.2, 69.1, 68.8, 62.2, The monobezoates were separated after a second flash column using silica gel. The 2-ester compound 40 was obtained in 12% yield, 1 H NMR (CDCl 3, 400MHz) δ 8.10 (m, 2H), (m, 3H), (m, 5H), 5.61 (s, 1H), 5.38 (dd, 1H, J = 10.3, 3.7 Hz), 5.12 (d, 1H, J = 3.7 Hz), (m, 2H), 4.29 (dd, 1H, J = 10.3, 3.7 Hz), 4.13 (dd, 1H, J = 1, 1.8 Hz), 3.81 (s, broad, 1H), 3.44 (s, 3H). 13 C NMR (CDCl 3, 100MHz) δ 166.6, 137.4, 133.2, 129.9, 129.7, 129.3, , , , 98.4, 76.2, 71.9, 69.2, 67.4, 6, The 3-ester compound 41 was obtained in 45% yield as the major product. 1 H NMR (CDCl 3, 400MHz) δ 8.10 (d, 1H, J = 7.7 Hz), (m, 8H), S10

11 4 (s, 1H), 5.39 (dd, 1H, J = 10.3, 3.3 Hz), 1(d, 1H, J = 3.7 Hz), 0 (d, 1H, J = 3.7 Hz), 4.34 (m, 2H), 4.11 (m, 1H), 3.81 (s, broad, 1H), 1 (s, 3H). 13 C NMR (CDCl 3, 100MHz) δ 166.8, 137.7, 133.3, 129.9, 129.8, 128.9, 128.4, 128.1, 12, 100.6, 100.4, 74.4, 72.1, 69.2, 66.9, 62.6, References: R1. Kondo, Y. Agric. Biol. Chem. 1977, 41, R2. Hoenig, H.; Weidman, H. Carbohydr. Res. 1975, 39, R3. Kim, S.; Chang, H.; Kim, W. J. J. rg. Chem. 1985, 50, R4. Vatele, J.-M. Tetrahedron, 2007, 63, R5. Horvath, A.; Ruttens, B.; Herdewijn, P. Tetrahedron Lett. 2007, 48, R6. Lu, X.-A.; Chou, C.-H.; Wang, C.-C.; Hung, S.-C. Synlett, 2003, ; R7. Kondo, Y. Carbohydr. Res. 1989, 193, R8. Wang, H.; She, J.; Zhang, L.-H.; Ye, X.-S. J. rg. Chem. 2004, 69, R9. Hu, G.; Vasella, A. HeIv. Chim. Acta, 2002, 85, R10. Gangadharmath, U. B.; Demchenko, A. V. Synlett, 2004, S11

12 Bz Figure 1a 1 H NMR spectrum of compound 20, 400MHz, CDCl 3, top is an expansion Figure 1b. 13 C NMR spectrum of compound 20, 100MHz, CDCl 3. S12

13 Bn H Figure 2a. 1 H NMR spectrum of compound 21 (starting material), 400MHz, CDCl Figure 2b. 1 H NMR spectrum of hydrolysis product from 22, 400MHz, CDCl 3. These two NMR spectra are identical to each other. The integration of Figure 2b is shown on the next page. S13

14 Figure 2b with integration. 1 H NMR spectrum of hydrolysis product from 22, 400MHz, CDCl 3. The top spectrum is the expansion of range 3-5ppm. S14

15 Bn Bz Figure 3a. 1 H NMR spectrum of compound 22, 400MHz, CDCl 3, top is an expansion Figure 3b. 13 C NMR spectrum of compound 22, 100MHz, CDCl 3. S15

16 H H Figure 4a. 1 H NMR spectrum of compound 23, 500MHz, CDCl 3, the top is an expansion Figure 4b. 13 C NMR spectrum of compound 23, 125MHz, CDCl 3. S16

17 H Bz Figure 5a. 1 H NMR spectrum of compound 24, 400MHz, CDCl 3, the top is an expansion Figure 5b. 13 C NMR spectrum of compound 24, 100MHz, CDCl 3. S17

18 Ac Bz 2.1 H-3 H Figure 6a. 1 H NMR spectrum of acetylated compound 24, 400MHz, CDCl 3, the top is an expansion Figure 6b. 13 C NMR spectrum of acetylated compound 24, 400MHz, CDCl 3. S18

19 H Bz Me H-1, d H-2, dd H Figure 7a. 1 H NMR spectrum of compound 25, 400MHz, CDCl 3, the top shows expansion Figure 7b. 13 C NMR spectrum of compound 25, 100MHz, CDCl 3. S19

20 PMP H H Me Figure 8a. 1 H NMR spectrum of compound 26, 400MHz, CDCl Figure 8b. 13 C NMR spectrum of compound 26, 100MHz, CDCl 3. S20

21 PMP H Bz Me 1.1 H-1 H-2 H Figure 9a. 1 H NMR spectrum of compound 27, 400MHz, CDCl 3, the top is an expansion Figure 9b. 13 C NMR spectrum of compound 27, 100MHz, CDCl 3. S21

22 H-1 H-1 of Figure 10. Crude 1 H NMR spectrum of compound 27, 400MHz, CDCl 3, using benzoic acid as the acylating agent. The top spectrum shows the expansion of ppm region, the peaks corresponding to the product s H-1 (5.1, dd) and starting material ( 4.8, dd) are labeled. The crude NMR spectrum indicated ~90% conversion. S22

23 26 27 H-1, 26 H-1, Figure 11. Crude 1 H NMR spectrum of compound 27, 400MHz, CDCl 3, using thiobenzoic acid as the acylating agent. The top spectrum shows the expansion of ppm region, the peaks corresponding to the product 27 and starting material 26 are labeled. The crude NMR spectrum indicated ~35% conversion. S23

24 H H Figure 12a. 1 H NMR spectrum of compound 29, 400MHz, CDCl Figure 12b. 13 C NMR spectrum of compound 29, 100MHz, CDCl 3. S24

25 H Bz H-2 H Figure 13a. 1 H NMR spectrum of compound 35, 400MHz, CDCl 3, top shows expansion Figure 13b. 13 C NMR spectrum of compound 35, 100MHz, CDCl 3. S25

26 Bz H 5.2 H-3 H Figure 14a. 1 H NMR spectrum of compound 36, 400MHz, CDCl 3, contain trace amount of EtAc, the top one is an expansion showing the protons at C-2 and C-3 carbons Figure 14b. 13 C NMR spectrum of compound 36, 100MHz, CDCl 3. S26

27 Bz H Me H-3 H Figure 15a. 1 H NMR spectrum of compound 39, 400MHz, CDCl 3, the top is an expansion, contain trace amount of hexane, water Figure 15b. 13 C NMR spectrum of compound 39, 100MHz, CDCl 3. S27

28 H Bz Me 2.1 H-2 H Figure 16a. 1 H NMR spectrum of compound 40, 400MHz, CDCl 3, the top is an expansion Figure 16b. 13 C NMR spectrum of compound 40, 100MHz, CDCl 3. S28

29 Bz Bz Me Figure 17a. 1 H NMR spectrum of compound 41, 400MHz, CDCl 3, contain trace amount of hexane, and water Figure 17b. 13 C NMR spectrum of compound 41, 100MHz, CDCl 3. S29

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