ChemInform Abstract: Efficient and Stereoselective 1,2-cis-Glycoside Formation of 5- Thioaldopyranoses: Glycosylation with Peracetylated 5-Thio-D- arabinopyranosyl and 5-Thio-L-fucopyranosyl Trichloroacetimidates

Trichloroacetimidate method was proved to be effective for 5-thio- D -arabinopyranosylation and 5-thio- L -fucopyranosylation of N -acetyl- D -glucosaminides and D -galactosides. In these 5-thioglycosylation the neighboring group participation of 2- O -acetyl function was not decisive of anomeric stereoselectivity to give 1,2- cis pseudodisaccharides predominantly. Allyl 2- O -(5-thio-α- L -fucopyranosyl)-β- D -galactopyranoside showed potent inhibitory activity towards α- L -fucosidase (Ki=30μM).