Journal article
Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine
Journal of organic chemistry, Vol.70(10), pp.4195-4198
2005
DOI: 10.1021/jo047812o
PMID: 15876119
Abstract
It is demonstrated that a ring-fused 2,3-oxazolidinone-protected derivative of 1-tolylthio-N-acetyl-D-glucosamine undergoes high-yield glycosidation under mild donor activation conditions. Stereoselective formation of α-linked or β-linked glycosides is dependent on reactivity of acceptor alcohols, where rate of glycosidation correlates to stereochemical outcome. Evidence for the role of glycosyl triflate intermediates and the N-acetyl substituent of the 2N,3O-oxazolidinone ring in stereochemical control is presented. © 2005 American Chemical Society.
Details
- Title: Subtitle
- Factors affecting stereocontrol during glycosidation of 2,3-oxazolidinone-protected 1-tolylthio-N-acetyl-D-glucosamine
- Creators
- PENG Wei - University of IowaRobert J Kerns - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.70(10), pp.4195-4198
- DOI
- 10.1021/jo047812o
- PMID
- 15876119
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Language
- English
- Date published
- 2005
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984365887802771
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