Protecting Groups in Carbohydrate Chemistry Influence on Stereoselectivity of Glycosylations 英文参考文献.docVIP

Molecules 2010, 15, 7235-7265; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Protecting Groups in Carbohydrate Chemistry: Influence on Stereoselectivity of Glycosylations Jian Guo and Xin-Shan Ye * State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No.38, Beijing 100191, China; E-Mail: guojian_521@ (J.G.) * Author to whom correspondence should be addressed; E-Mail: xinshan@; Tel.: +86 10 Fax: +86-10 Received: 5 September 2010 / Accepted: 15 October 2010 / Published: 20 October 2010 Abstract: Saccharides are polyhydroxy compounds, and their synthesis requires complex protecting group manipulations. Protecting groups are usually used to temporarily mask a functional group which may interfere with a certain reaction, but protecting groups in carbohydrate chemistry do more than protecting groups usually do. Particularly, protecting groups can participate in reactions directly or indirectly, thus affecting the stereochemical outcomes, which is important for synthesis of oligosaccharides. Herein we present an overview of recent advances in protecting groups influencing stereoselectivity in glycosylation reactions, including participating protecting groups, and conformation- constraining protecting groups in general. Keywords: protecting group; stereoselectivity; glycosylation; carbohydrate Abbreviations Ac acetyl ADMB Bac 4-acetoxy-2,2-dimethylbutanoyl bacillosamine Bn benzyl BSP Boc Bz 1-benzenesulfinylpiperidine tert-butoxycarbonyl benzoyl DCM DDQ dichloromethane 2,3-dichloro-5,6-dicyano-1,4-benzoquinone  Molecules 2010, 15 7236 DMBPP DMTM DTBMP DTBS FPsc 3-(2-hydroxyphenyl)-3,3-dimethylpropanoate 2,2-dimethyltrimethylene 2,6-di-tert-butyl-4-methylpyridine di-tert-butylsilylene fluorous propylsulfonylethoxycarbonyl hexyl Hex MP p-methoxyphenyl Msc NAP NIS methylsulfonyleth