1-Naphthylpropargyl Ether Group: A Readily Cleaved and Sterically Minimal Protecting System for Stereoselective Glycosylation
- 23 September 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (21) , 4879-4882
- https://doi.org/10.1021/ol061938l
Abstract
The (1-naphthyl)propargyl group is introduced as a sterically unobtrusive alcohol protecting group that is cleaved in a single step by exposure to dichlorodicyanoquinone in wet dichloromethane. In conjunction with the 4,6-O-benzylidene protecting group, and the use of the sulfoxide glycosylation method, 3-O-naphthylpropargyl-protected mannosyl donors are extremely β-selective.Keywords
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