SUPPLEMENTARY INFORMATION

Size: px
Start display at page:

Download "SUPPLEMENTARY INFORMATION"

Transcription

1 Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using chemical synthesis procedures outlined below. ML5 was also purchased from Chembridge. Scheme : Synthesis of ML5 Step : Preparation of N-[(,4-dichlorophenyl)methyl]-4-methanesulfonamidobenzamide (ML5) A 5 ml reaction bottle equipped with a magnetic stirbar was charged with,4-dichlorobenzylamine ( µl, mmol, equiv.), 4-(methanesulfonylamino)benzoic acid (6 g, mmol, equiv.) and N,N-dimethylformamide (. ml). To the mixture was added HATU (4 g,. mmol,.5 equiv.) followed by triethylamine ( ml,. mmol,. equiv.) The reaction mixture was stirred for hours at room temperature and then partitioned between ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, then dried over Na S 4, decanted, and concentrated. The crude residue was re-suspended in dichloromethane and purified by automated silica gel flash chromatography on a g silica gel cartridge, using gradient elution with -% of ethyl acetate in hexane. Pure fractions were collected and concentrated to afford 44 mg of the desired product N-[(,4-dichlorophenyl)methyl]-4-methanesulfonamidobenzamide (6. % yield). H NMR ( MHz, DMS-d6) δ ppm.7 (s, H) 4.49 (d, J=5.46 Hz, H) 7.6 (m, J=8.67 Hz, H) 7.4 (d, J=8.67 Hz, H) 7.4 (d, J=8. Hz, H) 7.6 (s, H) 7.89 (m, J=8.48 Hz, H) 8.99 (br. s., H) 5 (s, H) C NMR (75 MHz, DMS-d6) δ ppm 9.68, 44, 8., 7., 8.57, 8.66, 8.8,.,.7,.88, 5.7, 4.46,65.89 LCMS predicted: m/z: m/z: 7. (.%), 74. (69.%), 7. (7.9%), 76. (.%), 75. (.8%), 77. (.%), 76. (.5%), 74. (.%) seen: [M+H] + (major) 7., 74.9 also [M+CH CN+H] + (major) 4.9,

2 Scheme : Synthesis of ML4 Step : Preparation of -[-(4-chloro--methylphenoxy)ethyl]-,-dihydro-H-isoindole-,- dione The preparation of this known compound was based on that described. A solution of diethyl azodicarboxylate (.58 ml, 7.8 mmol,.5 equiv.) in dry THF (5 ml) was added under dry nitrogen to a solution of -(4-chlorophenoxy) ethylamine ( g, 5. mmol, equiv.), triphenylphosphine (.6 g, 7.8 mmol,.5 equiv.) and 4-chloro--methylphenol (.9 g, 7.8 mmol,.5 equiv.) in dry THF (5 ml). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was re-suspended in diethyl ether and the solid filtered off on Celite. The filtrate was concentrated and the residue was re-dissolved in dichloromethane and then purified by silica gel chromatography on an 8 g silica gel cartridge using gradient elution with -% ethyl acetate in hexane to afford g of the desired product - [- (4-chloro--methylphenoxy)ethyl] -,-dihydro-h isoindole-,-dione (56 % yield). Step : Preparation of -(-aminoethoxy)-4-chloro--methylbenzene Deprotection of the amine function was accomplished according to the procedure described in. A 5 ml reaction bottle with a magnetic stir bar was charged with -[-(4-chloro--methylphenoxy)ethyl],-dihydro-H-isoindole-,-dione (47 mg,. mmol, equiv.) and methanol ( ml) was added, followed by hydrazine monohydrate (5 µl, mmol, 7.8 equiv.). The reaction mixture was stirred for 7 hours at room temperature after which time the reaction was judged complete. The solvent was evaporated chloroform was added, the organic layer was washed with water and brine and then dried over Na S 4, decanted, and concentrated. The residue was re-suspended in dichloromethane and applied purified by silica gel chromatography on a g silica gel cartridge using gradient elution -% of % NH 4 H in methanol in dichloromethane to afford 79 mg of the desired product ( aminoethoxy) 4 chloro methylbenzene ( % yield).

3 H NMR ( MHz, CHLRFRM-d) δ ppm.9 (s, H).9 (t,j=4.9 Hz, H).4 (s, H).95 (t, J=5.9 Hz, H) 6.7 (d, J=8.9 Hz, H) (m, H) C NMR (75 MHz, CHLRFRM-d) δ ppm 6.45, 4.8, 79,.9, 5.5, 6.7, 8.94, 6, 55.8 LCMS (done on crude reaction mixture), predicted: m/z: 85.6 (.%), 87.6 (.%), 86.6 (%), 88.6 (.%) seen: [M+H] + (major) = 86., also [M+CH CN+H] + 7., 9. Step : Preparation of N-[-(4-chloro--methylphenoxy)ethyl]thiophene--carboxamide (ML4) A 5 ml reaction bottle with a magnetic stirbar was charged with ( aminoethoxy) 4 chloro methylbenzene (9 mg, mmol, equiv.), thiophene--carboxylic acid (7 mg, mmol, equiv.) and N,N-dimethylformamide (. ml, 5.9 mmol,.4 equiv.). To the mixture was added added HATU ( mg, mmol,.5 equiv.) followed by triethylamine (89 µl, mmol,. equiv.) The reaction mixture was stirred for hours at room temperature and then partitioned between ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, then dried over Na S 4, decanted, and concentrated. The residue was re-suspended in dichloromethane and purified by automated silica gel flash chromatography on a g silica gel cartridge, using gradient elution with -% of ethyl acetate in hexane. The resulting residue (8.5mg) was further purified by preparative HPLC (C8 column, 4% to 9% methanol in water,.5% formic acid) to afford mg of the desired product N-[-(4-chloro--methylphenoxy)ethyl]thiophene--carboxamide (9 % yield). H NMR ( MHz, CHLRFRM-d) δ ppm.4 (s, H).89 (q, J=5.7 Hz, H) 4.4 (t, J=5.5 Hz, H) 6.48 (br. s., H) 6.76 (d, J=8. Hz, H) (m, H) 7.5 (d, J=5.9 Hz, H) 7.54 (d, J=.58 Hz, H) C NMR (75 MHz, CHLRFRM-d) δ ppm 6.8, 9.9, 67.8,., 5.66, 6.5, 7.69, 8.5, 8.49,.6, 4, 8.45, 55.8, 6.95 LCMS predicted: m/z: 95.4 (.%), 97.4 (6.5%), 96.5 (5.4%), 98.4 (5.9%), 99.4 (.7%), 97.5 (.6%), 96.4 (.%) seen: [M+H] + (major) 96., 98.

4 Scheme : Synthesis of ML5a Step : Preparation of trans tert butyl N-(4-{[(,4- dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate A round bottom flask was charged with Boc-trans-,4-aminocyclohexane carboxylic acid (8 mg, mmol, equiv.) and N,N-dimethylformamide (5 ml). To the mixture was added added HATU (44 mg,. mmol,.5 equiv.) followed by,4-dichlorobenzylamine ( µl, mmol, equiv.), and finally triethylamine ( ml,. mmol,. equiv.). The reaction mixture was stirred for an hour at room temperature and then diluted with ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, leading to the formation of a precipitate. The entire two-phase mixture was therefore filtered and the precipitate collected on a paper filter. This afforded the product, trans tert butyl N-(4-{[(,4-dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate (57 mg, mmol, 86%), which was used in the next step without further purification. H NMR ( MHz, CHLRFRM-d) δ ppm. (dd, J=.87,.9 Hz, H).44 (s, 8 H).57 (dd, J=.4,. Hz, H).9 (d, J=.8 Hz, H) (m, H) 4.47 (d, J=6. Hz, H) 5.9 (br. s., H) 7. (dd, J=8.9,.98 Hz, H) 7. (d, J=8.9 Hz, H) 7.8 (d, J=.7 Hz, H) LCMS: predicted: m/z: 4 (.%), 4. (64.%), 4.4 (%), 4 (.7%), 44. (%), 4.4 (.7%), 45. (.%), 44.4 (.%) Seen: (only fragment, m-5 observed (major): 86., 88. Step : Preparation of trans-4-amino-n-[(,4-dichlorophenyl)methyl]cyclohexane-- carboxamide hydrochloride A 5 ml round-bottom flask was charged with trans tert butyl N (4 {[(,4 dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate (57 mg, mmol) dissolved in dichloromethane (4. ml) with stirring, and then treated with a hydrochloric acid solution (4. ml of 4M 4

5 solution in,4 dioxane, 6. mmol, 5. equiv.). The reaction mixture was stirred overnight and then the solvent was evaporated to afford crude trans-4 amino N [(,4 dichlorophenyl)methyl]cyclohexane carboxamide hydrochloride (44 mg, mmol), which was used in the next step without further purification. H NMR ( MHz, DMS-d6) δ ppm (m, 4 H).8 (d, J=.6 Hz, H). (d, J=9.6 Hz, H).9 (m., H).95 (br. s., H) 4.7 (d, J=5.7 Hz, H) 7. (d, J=8.9 Hz, H) 7.4 (d, J=8.85 Hz, H) 7.6 (s, H) 8.5 (br. s., H) 8.46 (t, J=5.5 Hz, H) LCMS, predicted: m/z:.8 (.%),.8 (64.%), 8 (5.9%), 4.7 (%),.8 (9.8%), 5.8 (.6%),.9 (.%) seen: [M+H] + (major) = 9,.9 Step : Preparation of trans-n-[(,4-dichlorophenyl)methyl]-4-ethenesulfonamidocyclohexane- -carboxamide A 5 ml round bottom flask was charged with trans-4 amino N [(,4 dichlorophenyl)methyl]cyclohexane carboxamide hydrochloride (5 mg, mmol,. equiv.) dissolved in dichloromethane (.5 ml). The mixture was stirred in an ice bath and treated with triethylamine (.8 ml, mmol, 5. equiv.), followed by methanesulfonyl chloride (9 µl, mmol, equiv.). The reaction mixture was stirred for hours while warming to room temperature. During the reaction a precipitate formed, and this was collected by vacuum filtration on a paper filter. The solid was saved and the filtrate was applied directly on a g silica gel cartridge and purified using gradient elution (-% ethyl acetate in hexanes). Relevant fractions were collected and concentrated to afford 9.5 mg of the product, which was identical to the precipitate collected directly from the reaction mixture. Combined, this amounted to 9 mg of the desired product, trans-n-[(,4-dichlorophenyl)methyl]-4-ethenesulfonamidocyclohexane--carboxamide ( mmol, 9% over two steps). H NMR ( MHz, DMS-d6) δ ppm. (m, H).4 (m H).76 (d, J=6 Hz, H).9 (d, J=9. Hz, H).-. (m, H).89 (s, H) (m, H) 4.5 (d, J=5.84 Hz, H) 6.98 (d, J=7.54 Hz, H) 7.6 (d, J=8. Hz, H) 7.4 (dd, J=8.8,.7Hz, H) 7.59 (d, J=.7 Hz, H) 8.9 (t, J=5.5 Hz, H) C NMR ( MHz, DMS-d6) δ ppm 8.9,.9, 9.8, 4, 4.7, 5.49, 7., 8.5, 9.9,.8,.89, 5.77, 74.9 LCMS: Predicted: m/z: 78.6 (.%), 8.5 (68.4%), 79.6 (7.4%), 8.5 (.%), 86 (.5%), 8.5 (.%), 8.6 (.%), 8.6 (.4%), 85 (%), observed (m/z): [M+H] + = (major) 79.,

6 References. Pascale, R. et al. New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards alpha-glucosidase. Bioorg Med Chem 8, , doi:6/j.bmc ().. Eguchi, Y., Sasaki, F., Sugimoto, A., Ebisawa, H. & Ishikawa, M. Studies on Hypotensive Agents - Synthesis of -Substituted -(-Chlorophenyl)-6-Ethoxycarbonyl-5,7-Dimethyl-,4(h,h)- Quinazolinediones. Chem Pharm Bull 9, (99). 6

7 ML5- H NH 5 9 S CH 5 NH ML5- C

8 ML5- C solvent region NH 5 9 S CH NH ML5- C aryl region

9 5 5 ML4- H 7 S 6 5 NH CH ML4- C

10 ML4- C alkyl region 7 S NH CH ML4- C aryl region

11 ML5a- H S 8 NH NH ML5a- C

12 ML5a- C alkyl region 9 S 8 NH NH ML5a- C aryl region

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian

All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature24451 Chemical synthesis of USP7 compounds General 1 H, 13 C and 19 F nuclear magnetic resonance (NMR) spectra were obtained on either Bruker or Varian spectrometers at 300 or 400 MHz,

More information

Supporting 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 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 information

Supporting Information for

Supporting 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 information

Supplementary 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) 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 information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An 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 information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi:10.1038/nature22309 Chemistry All reagents and solvents were commercially available unless otherwise noted. Analytical LC-MS was carried out using a Shimadzu LCMS-2020 with UV detection monitored between

More information

Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions

Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Supporting Information for: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions Patrick S. Fier* and Kevin M. Maloney* S1 General experimental details All reactions

More information

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.

Fast 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 information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Supporting Information

Supporting Information Supporting Information An L-proline Functionalized Metallo-organic Triangle as Size-Selective Homogeneous Catalyst for Asymmertry Catalyzing Aldol Reactions Xiao Wu, Cheng He, Xiang Wu, Siyi Qu and Chunying

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis 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 information

Supporting Information

Supporting Information Supporting Information Syntheses and characterizations: Compound 1 was synthesized according to Scheme S-1. Scheme S-1 2 N N 5 i N 4 P Et Et iii N 6 ii P Et Et iv v, vi N N i) Fmoc-Su, DIPEA, Acetone;

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting 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 information

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy

Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted

More information

Supplementary Information

Supplementary 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 information

Accessory Information

Accessory Information Accessory Information Synthesis of 5-phenyl 2-Functionalized Pyrroles by amino Heck and tandem amino Heck Carbonylation reactions Shazia Zaman, *A,B Mitsuru Kitamura B, C and Andrew D. Abell A *A Department

More information

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan

More information

(Supplementary Information)

(Supplementary Information) (Supplementary Information) Peptidomimetic-based Multi-Domain Targeting Offers Critical Evaluation of Aβ Structure and Toxic Function Sunil Kumar 1*, Anja Henning-Knechtel 2, Mazin Magzoub 2, and Andrew

More information

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of

More information

Supporting Information. Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling

Supporting Information. Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling Supporting Information Visualization of Phagosomal Hydrogen Peroxide Production by A Novel Fluorescent Probe That Is Localized via SNAP-tag Labeling Masahiro Abo, Reiko Minakami, Kei Miyano, Mako Kamiya,

More information

Supporting Information

Supporting 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 information

Supporting Information For:

Supporting Information For: Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003 Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,

More information

Supporting Information:

Supporting 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 information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications This journal is The Royal Society of Chemistry 2012

Electronic 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 information

Simplified platensimycin analogues as antibacterial agents

Simplified platensimycin analogues as antibacterial agents Simplified platensimycin analogues as antibacterial agents Dragan Krsta, a Caron Ka, a Ian T. Crosby, a Ben Capuano a and David T. Manallack a * a Medicinal Chemistry and Drug Action, Monash Institute

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

New Substrates and Enzyme Assays for the Detection of Mucopolysaccharidosis III (Sanfilippo Syndrome) Types A, B, C and D by Tandem Mass Spectrometry

New Substrates and Enzyme Assays for the Detection of Mucopolysaccharidosis III (Sanfilippo Syndrome) Types A, B, C and D by Tandem Mass Spectrometry Supporting Information for: New Substrates and Enzyme Assays for the Detection of Mucopolysaccharidosis III (Sanfilippo Syndrome) Types A, B, C and D by Tandem Mass Spectrometry Brian J. Wolfe, Farideh

More information

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template

Supporting Information. Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Supporting Information Rh (III)-Catalyzed Meta-C H Olefination Directed by a Nitrile Template Hua-Jin Xu, Yi Lu, *, Marcus E. Farmer, Huai-Wei Wang, Dan Zhao, Yan-Shang Kang, Wei-Yin Sun, *, Jin-Quan Yu

More information

2017 Reaction of cinnamic acid chloride with ammonia to cinnamic acid amide

2017 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 information

Electronic Supplementary Information for

Electronic Supplementary Information for Electronic Supplementary Information for Sequence Selective Dual-Emission Detection of (i, i+1) Bis-Phosphorylated Peptide Using Diazastilbene-Type Zn(II)-Dpa Chemosensor Yoshiyuki Ishida, Masa-aki Inoue,

More information

Supplementary Note 2. Synthesis of compounds. Synthesis of compound BI Supplementary Scheme 1: Synthesis of compound BI-7273

Supplementary Note 2. Synthesis of compounds. Synthesis of compound BI Supplementary Scheme 1: Synthesis of compound BI-7273 Supplementary ote 2 Synthesis of compounds Synthesis of compound I-7273 H HMe 2 *HCl aac, AcH 4 7 ah(ac) 3 ah, MeI CH 2 Pd 2 (dba) 3, KAc, X-Phos 1,4-dioxane 5 6 8 + Pd(dppf) *CH 2 a 2 C 3 DMF I-7273 (2)

More information

Electronic Supplementary Material

Electronic 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 information

Table of Contents for Supporting Information

Table of Contents for Supporting Information Table of Contents for Supporting Information General... S2 General Pd/Cu Coupling Reaction Procedures... S2 General Procedure for the Deprotection of Trimethylsilyl-Protected Alkynes.... S3 2,5-Dibromo-1,4-diiodobenzene

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Supporting Information

Supporting Information Supporting Information for Macromol. Chem. Phys, DOI: 10.1002/macp.201700302 Phase Segregation in Supramolecular Polymers Based on Telechelics Synthesized via Multicomponent Reactions Ansgar Sehlinger,

More information

(Supplementary Information)

(Supplementary Information) Foldamer-mediated Structural Rearrangement Attenuates Aβ Oligomerization and Cytotoxicity (Supplementary Information) Sunil Kumar* 1, Anja Henning-Knechtel 2, Ibrahim Chehade 2, Mazin Magzoub 2, and Andrew

More information

Supporting Information:

Supporting Information: Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The 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 information

Scalable 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 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 information

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks Mintu Porel and Christopher A. Alabi* School of Chemical and Biomolecular Engineering, Cornell University, Ithaca, New York 14853,

More information

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection

Block: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

An efficient one pot ipso-nitration: Structural transformation of a dipeptide by N-terminus modification

An efficient one pot ipso-nitration: Structural transformation of a dipeptide by N-terminus modification Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supporting information An efficient one pot ipso-nitration: Structural transformation of a

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting 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 information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Content Synthesis of compounds 2a, 2b in Scheme

More information

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker

Kinetics experiments were carried out at ambient temperature (24 o -26 o C) on a 250 MHz Bruker Experimental Materials and Methods. All 31 P NMR and 1 H NMR spectra were recorded on 250 MHz Bruker or DRX 500 MHz instruments. All 31 P NMR spectra were acquired using broadband gated decoupling. 31

More information

Supporting Information for

Supporting Information for Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones 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 information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Coupling 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.

Coupling 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 information

Compound Number. Synthetic Procedure

Compound Number. Synthetic Procedure Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC

More information

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0

More information

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

Supporting 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 information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

SUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles

SUPPORTING INFORMATION. in the Synthesis of Fluorenones and ortho-arylated. Benzonitriles SUPPRTING INFRMATIN Carbon-Hydrogen Bond Functionalization Approach in the Synthesis of Fluorenones and ortho-arylated Benzonitriles Dmitry Shabashov, Jesús R. Molina Maldonado and lafs Daugulis* Department

More information

SUPPORTING INFORMATION

SUPPORTING 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 information

Ring-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols

Ring-Opening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Ring-pening / Fragmentation of Dihydropyrones for the Synthesis of Homopropargyl Alcohols Jumreang Tummatorn, and Gregory B. Dudley, * Department of Chemistry and Biochemistry, Florida State University,

More information

Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information

Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig M. Williams Supporting Information General Methods S-2 Experimental S-2 1 H and 13 C NMR Spectra S-7 Comparison:

More information

Supporting Information

Supporting 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 information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.

Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,

More information

RNA-Ligand Interactions: Affinity and Specificity of Aminoglycoside Dimers and Acridine Conjugates to the HIV-1 Rev Response Element

RNA-Ligand Interactions: Affinity and Specificity of Aminoglycoside Dimers and Acridine Conjugates to the HIV-1 Rev Response Element RA-Ligand Interactions: Affinity and pecificity of Aminoglycoside Dimers and Acridine Conjugates to the HIV-1 Rev Response Element athan W. Luedtke, Qi Liu, and Yitzhak Tor* *Department of Chemistry and

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

Synthesis 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 information

Supporting Information

Supporting Information Supporting Information Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers Jian-Bo Liu, Xiu-Hua Xu, and Feng-Ling Qing Table of Contents 1. General Information --------------------------------------------------------------------------2

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis

Synthesis 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 information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Effect of polymer chain conformation on field-effect transistor performance: synthesis and properties of two arylene imide based D-A copolymers Dugang Chen, a Yan Zhao,

More information

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer

Aminoacid Based Chiral N-Amidothioureas. Acetate Anion. Binding Induced Chirality Transfer Aminoacid Based Chiral -Amidothioureas. Acetate Anion Binding Induced Chirality Transfer Fang Wang, a Wen-Bin He, a Jin-He Wang, a Xiao-Sheng Yan, a Ying Zhan, a Ying-Ying Ma, b Li-Cai Ye, a Rui Yang,

More information

Supporting Information

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 217 Electronic Supplementary Material

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Enantioselective Synthesis of Axially Chiral Vinyl arenes through Palladium-catalyzed

More information

Domino 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 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 information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Visible light-mediated dehydrogenative

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany SUPPRTIG MATERIAL Base Dependence in Copper-catalyzed Huisgen Reactions: Efficient Formation of Bistriazoles Yu Angell and Kevin Burgess *

More information

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and

Supporting Information. A rapid and efficient synthetic route to terminal. arylacetylenes by tetrabutylammonium hydroxide- and Supporting Information for A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3- butyn-2-ols Jie Li and

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Supporting Information

Supporting Information Electronic upplementary Material (EI) for rganic Chemistry rontiers. This journal is the Partner rganisations 0 upporting Information Convenient ynthesis of Pentafluoroethyl Thioethers via Catalytic andmeyer

More information

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas, Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department

More information

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,

More information

Electronic Supplementary Information

Electronic Supplementary Information S1 Electronic Supplementary Information Direct Aerobic Oxidation of 2-Benzylpyridines in a Gas- Liquid Continuous-Flow Regime Using Propylene Carbonate as Solvent Bartholomäus Pieber and C. Oliver Kappe*

More information

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe

Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments

More information

ELECTRONIC SUPPLEMENTARY INFORMATION FOR. Cyclizations and Cycloadditions of Acetylenic Sulfones on Solid Supports. Thomas G. Back* and Huimin Zhai

ELECTRONIC SUPPLEMENTARY INFORMATION FOR. Cyclizations and Cycloadditions of Acetylenic Sulfones on Solid Supports. Thomas G. Back* and Huimin Zhai Supplementary Material (ESI) for Chemical Communications 1 ELECTRONIC SUPPLEMENTARY INFORMATION FOR Cyclizations and Cycloadditions of Acetylenic Sulfones on Solid Supports Thomas G. Back* and Huimin Zhai

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence

More information

Minoru Tanaka 1,2,#, Justin M. Roberts 1,#, Hyuk-Soo Seo 3, Amanda Souza 1, Joshiawa Paulk 1,

Minoru Tanaka 1,2,#, Justin M. Roberts 1,#, Hyuk-Soo Seo 3, Amanda Souza 1, Joshiawa Paulk 1, Design and Characterization of Bivalent BET Inhibitors Minoru Tanaka 1,2,#, Justin M. Roberts 1,#, Hyuk-Soo Seo 3, Amanda Souza 1, Joshiawa Paulk 1, Thomas G. Scott 1, Stephen L. DeAngelo 1,3, Sirano Dhe-Paganon

More information

Supporting material for Chiral Sensing using a Blue Fluorescent Antibody

Supporting material for Chiral Sensing using a Blue Fluorescent Antibody Supporting material for Chiral Sensing using a Blue Fluorescent Antibody ana Matsushita, oboru Yamamoto, Michael M. ijler, Peter Wirsching, Richard A. Lerner, Masayuki Matsushita and Kim D. Janda Synthesis

More information

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric

Supplementary Information. for. Stable Supramolecular Helical Structure of C 6 -Symmetric Supplementary Information for Stable Supramolecular Helical Structure of C 6 -Symmetric Hydrogen-Bonded Hexakis(phenylethynyl)benzene Derivatives with Amino Acid Pendant Groups and Their Unique Fluorescence

More information

Supporting Information

Supporting Information Supporting Information An Extremely Active and General Catalyst for Suzuki Coupling Reactions of Unreactive Aryl Chlorides Dong-Hwan Lee and Myung-Jong Jin* School of Chemical Science and Engineering,

More information

Aziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine

Aziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information (ESI) Aziridine in Polymers: A Strategy to Functionalize

More information

Enantioselective Organocatalytic Michael Addition of Malonate Esters to Nitro Olefins Using Bifunctional Cinchonine Derivatives

Enantioselective Organocatalytic Michael Addition of Malonate Esters to Nitro Olefins Using Bifunctional Cinchonine Derivatives Enantioselective rganocatalytic Michael Addition of Malonate Esters to itro lefins Using Bifunctional Cinchonine Derivatives Jinxing Ye, Darren J. Dixon * and Peter S. Hynes School of Chemistry, University

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS 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 information

Supporting Information

Supporting Information Supporting Information Synthesis of the natural product Marthiapeptide A Yuqi Zhang 1, Md. Amirul Islam 1 and Shelli R. McAlpine 1* 1 School of Chemistry, University of New South Wales, Sydney, NSW 2052

More information

Supplementary Note 1: Synthetic Chemistry Procedures

Supplementary Note 1: Synthetic Chemistry Procedures Supplementary Note 1: Synthetic Chemistry Procedures Structure-inspired design of β-arrestin-biased ligands for aminergic GPCRs John D. McCorvy 1 *, Kyle V. Butler 2 *, Brendan Kelly 3*, Katie Rechsteiner

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information for uminum complexes containing salicylbenzoxazole

More information

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.

dichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere. Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with

More information