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Science China Chemistry

, Volume 54, Issue 1, pp 66–73 | Cite as

Pre-activation based stereoselective glycosylations: Stereochemical control by additives and solvent

  • Gilbert Wasonga
  • YouLin Zeng
  • XueFei HuangEmail author
Articles SPECIAL TOPIC The Frontiers of Chemical Biology and Synthesis

Abstract

Stereochemical control is an important issue in carbohydrate synthesis. Glycosyl donors with participating acyl protective groups on 2-O have been shown to give 1,2-trans glycosides reliably under the pre-activation based reaction condition. In this work, the effects of additives and reaction solvents on stereoselectivity were examined using donors without participating protective groups on 2-O. While several triflate salt additives did not have major effects, the amount of AgOTf was found to significantly impact the reaction outcome. Excess AgOTf led to lower stereochemical control presumably due to its coordination with the glycosyl triflate intermediate and a more SN1 like reaction pathway. In contrast, the stereoselectivity could be directed by reaction solvents, with diethyl ether favoring the formation of β-glycosides and dichloromethane leading to β isomers. The trend of stereochemical dependence on reaction solvent was applicable to a variety of building blocks including the selective formation of β-mannosides.

Keywords

stereoselectivity pre-activation based glycosylation additives solvent effects 

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Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryMichigan State UniversityEast LansingUSA

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