Syntheses of spacer-armed carbohydrate model compounds

Abstract

Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of d-glucose, N-acetyl- d-glucosamine and 3- O-methyl- d-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of ‘2-OH-compounds’ (such as 9-hydroxynonyl 3,4,6-tri- O-acetyl-β- d-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl β- d-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the 1H and 13C NMR spectra. © 1997 Elsevier Science Ltd.