Preparation of benzyl ethers of 1,2-dideoxy-2′-methyl-α-D-glucopyranoso-[2,1-d]-Δ2′-oxazoline for use in oligosaccharide synthesis

Abstract

Three benzyl ethers of 1,2-dideoxy-2′-methyl-α-D-glucopyranoso[2,1-d]-Δ²′-oxazoline (14) were prepared. High yield β-acetylation of suitably protected derivatives of 2-acetamido-2-deoxy-D-glucopyranose made the use of Matta's method convenient for synthesizing two isomeric acetylated di-O-benzyl ethers of (14), and the tri-O-benzyl ether was obtained by conventional benzylation of (14). The reactivity of the substituted oxazolines was tested through the preparation of various derivatives of 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D-gal-actopyranose (19).