1-naphthylpropargyl ether group: a readily cleaved and sterically minimal protecting system for stereoselective glycosylation.

ABSTRACT: [reaction: see text] 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 beta-selective.

SUBMITTER: Crich D 

PROVIDER: S-EPMC2615467 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature