Syntheses of spacer-armed carbohydrate model compounds

Article abstract of DOI:10.1016/S0008-6215(96)00256-X

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.