Application of the 4-trifluoromethylbenzenepropargyl ether group as an unhindered, electron deficient protecting group for stereoselective glycosylation.
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.
Crich
David
D
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
Karatholuvhu
Maheswaran S
MS
D004987:Ethers / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
C531445:4-trifluoromethylbenzenepropargyl ether; D004987:Ethers; D010293:Pargyline