A New, Powerful Glycosylation Method: Activation of Thioglycosides with Dimethyl Disulfide−Triflic Anhydride
- 1 October 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (22) , 4647-4650
- https://doi.org/10.1021/ol702139u
Abstract
Dimethyl disulfide reacts with triflic anhydride to provide a highly reactive electrophile. Various thioglycosides, differing in their thio aglycons, carbohydrate units, and protecting group pattern, were activated with Me2S2−Tf2O in the presence of different glycosyl acceptors. The reactions proceeded at low temperatures within a short time, affording oligosaccharides in high yields both on primary and secondary hydroxyls. Armed and disarmed glycosyl donors were activated equally efficiently.Keywords
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