N,N-Diacetylsialyl chloride--a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter.
N,N-Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles to give the corresponding alpha-glycosyl phosphate, beta-glycosyl dibenzyl phosphate, alpha-glycosyl azide, alpha-phenyl thioglycoside and alpha-glycosyl xanthate in 65-82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with alpha-configuration and highly efficient synthesis of beta-configured sialic acid glycosyl dibenzyl phosphate.
Orlova
Anna V
AV
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp. 47, Moscow, Russian Federation.
Shpirt
Anna M
AM
Kulikova
Nadezhda Y
NY
Kononov
Leonid O
LO
D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D006027:Glycosides; D019158:N-Acetylneuraminic Acid