Glucofuranosylation with penta-O-propanoyl-beta-D-glucofuranose.
Readily available, crystalline penta-O-propanoyl-beta-D-glucofuranose is shown to be a suitable glycosylating agent for the acid-catalysed, direct synthesis of O-, S- and N-glucofuranosyl compounds. Beta-linked products are formed with good selectivity. Reaction with cyanotrimethylsilane gave the 1,2-O-(1-cyanopropylidene)acetal rather than the C-glycosyl cyanide. By selective acid-catalysed hydrolysis, the title compound was converted to the 1-hydroxy analogue from which the trichloroacetimidates were made as further potential glycosylating agents.
Furneaux
Richard H
RH
Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand.
Martin
Bénédicte
B
Rendle
Phillip M
PM
Taylor
Carol M
CM
D000081:Acetamides; D062845:Chloroacetates; D005663:Furans; D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy
D000081:Acetamides; D062845:Chloroacetates; D005663:Furans; D005960:Glucosides; C475344:penta-O-propanoyl-glucofuranose; C009528:trichloroacetamide