A new method for the synthesis of aldehyde-spacered oligosaccharides by oxidation of l-tartaric acid derivative

Abstract

N-(N-[(2R,3R)-2,3-Dihydroxy-3-carboxypropionyl]glycyl)-β-d-glycopyranosylamines and N-[N-(formylcarbonyl)glycyl]-β-d-glycopyranosylamines, derivatives of lactose, human milk tri-, tetra-, and pentasaccharides, and synthetic di- and trisaccharides, were synthe- sized. N-Glycyl-β-d-glycopyranosylamines of these oligosaccharides were N-acylated with (+)-di-O-acetyl-l-tartaric anhydride, and the derivatives with α-glycol and terminal carboxy groups in the aglycon moiety were obtained after O-deacylation (70—80% yield). The short-term (80 s) selective oxidation of the α-glycol group of the tartaric acid residue in these derivatives with dilute periodic acid gave the target compounds with the terminal aldehyde group in aglycon in ~90% yield.