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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.

journal of organic chemistry

Application of the 4-Trifluoromethylbenzenepropargyl Ether Group as an Unhindered, Electron Deficient Protecting Group for Stereoselective Glycosylation