carbohydrate nitrone and nitrile oxide cycloaddition ... · carbohydrate nitrone and nitrile oxide...

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Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu Mukherjee, Sukhendu B. Mandal* and Anup Bhattacharjya* Chemistry Department, Indian Institute of Chemical Biology (a unit of CSIR), 4, Raja S. C. Mullick Road, Kolkata 700032, India Email: [email protected] ; [email protected] [email protected] SUPPLEMENTARY MATERIAL S1 Electronic Supplementary Material (ESI) for RSC Advances This journal is © The Royal Society of Chemistry 2012

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Page 1: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

Carbohydrate nitrone and nitrile oxide cycloaddition

approach to chiral sulfur heterocycles and nucleosides

Subhrangshu Mukherjee, Sukhendu B. Mandal* and Anup Bhattacharjya*

Chemistry Department, Indian Institute of Chemical Biology (a unit of CSIR), 4,

Raja S. C. Mullick Road, Kolkata 700032, India

Email: [email protected]; [email protected]

[email protected]

SUPPLEMENTARY MATERIAL

S1

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 2: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S2

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 3: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S3Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 4: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S4Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 5: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S5Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 6: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S6Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 7: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S7Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 8: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S8Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 9: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S9Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 10: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S10Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 11: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S11Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 12: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S12Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 13: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S13Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 14: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S14Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 15: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S15Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 16: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S16Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 17: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S17

Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 18: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S18Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 19: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S19Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 20: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S20Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 21: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S21Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 22: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S22Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 23: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S23Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 24: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S24Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 25: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S25Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 26: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S26Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 27: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S27Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 28: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S28Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 29: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S29Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 30: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S30Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 31: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S31Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 32: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S32Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 33: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S33Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 34: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S34Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 35: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S35Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 36: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S36Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012

Page 37: Carbohydrate nitrone and nitrile oxide cycloaddition ... · Carbohydrate nitrone and nitrile oxide cycloaddition approach to chiral sulfur heterocycles and nucleosides Subhrangshu

S37Electronic Supplementary Material (ESI) for RSC AdvancesThis journal is © The Royal Society of Chemistry 2012