Synthesis of β-d-(1→4)-Substituted Trehalose Oligosaccharides

Abstract

Glycosylation of 2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (5) with α-D-glucopyranosyl, α-maltosyl, and α-maltotriosyl bromides 4, 7, and 8 afforded the β-D-(1→4)-substituted trehalose tri-, tetra-, and pentasaccharides 6, 9, and 10 which were fully characterized by ¹H NMR spectroscopy. Deprotection gave the free oligosaccharides 1, 2, and 3.

Notes

Summer student 1988 from the University of Münster, Germany. Present address: Dr. Niggemann J., University of Washington, Department of Chemistry BG-10, Seattle, WA 98195, USA.

In the reaction of 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl trichloro-acetimidate with a symmetrical trehalose glycosyl acceptor a derivative of β-d-Glc-(1→4)-α,α-Tre was also obtained as a by-product in low yield.²