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Schmidt Glycosylation

(Schmidt Glycosidation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr565

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Schmidt Glycosylation. Comprehensive Organic Name Reactions and Reagents. 565:2498–2502.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Schmidt glycosylation is a Lewis acid-catalyzed glycosylation using glycosyl trichloroacetimidate as the donor. Presently, it is one of the most popular methods for glycosylation, second only to the glycosylation with a thioglycoside donor. The popularity of this reaction in carbohydrate transformations may be ascribed to the mildly acidic coupling conditions and the opportunities to alter α/β selectivity via different glycosyl trichloroacetimidate donors and/or the coupling reagents. Various mild acids compatible with this glycosylation reaction have been presented. In addition, the general 1,2-trans selectivity of glycosylation also applicable to this reaction. This reaction is useful to study the carbohydrate transformation.

Keywords:

  • glycosylation;
  • mild acids;
  • α-glycosyl trichloroacetimidate;
  • BF3·Et2O promoter