Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation.

ABSTRACT: 4-Trifluoromethylbenzenepropargyl ethers are stable and sterically minimal alcohol protecting groups that are readily cleaved in a single step by exposure to lithium naphthalenide. In conjunction with the 4,6-O-benzylidene protecting group, glycosylation reactions of 2-O-(4-trifluoromethylbenzenepropargyl)-protected mannosyl donors are extremely beta-selective.

SUBMITTER: Crich D 

PROVIDER: S-EPMC2742709 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature