Automated Parallel Synthesis of a Protected Oligosaccharide Library Based upon the Structure of Dimeric Lewis X by One-Pot Sequential Glycosylation

Abstract

An efficient synthesis of a protected dimeric Lewis X epitope by two sequential one-pot glycosylations is described. Combinatorial synthesis of the dimeric Lewis X epitope derivatives by the one-pot glycosylation was accomplished utilizing an automated synthesizer to provide 12-protected oligosaccharides.

Key words

automated synthesis - glycosyl fluoride - Lewis X - one-pot glycosylation - thioglycoside

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1

Current address: Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Aoba-ku, Sendai 980-8578, Japan; e-mail: [e-mail].

2

Current address: Department of Chemistry, Faculty of Science Okayama University of Science, Okayama, Ridai 1-1, Okayama 700-0005, Japan; e-mail: [e-mail].

14

Activation of the glycosylated thioglycoside using NIS/TfOH instead of DMTST resulted in decomposition of the resulting glycosyl fluoride 8.

15

The trisaccharide 12 was prepared by a linear type one-pot glycosylation using 3, 6, and 7, followed by acetylation of the resulting hydroxyl group.

16

L-COS^® is purchased from Moritex Corporation, Japan.

17

We have already reported the utility of the automated synthesizer for the parallel synthesis of oligosaccharides based on the structure of a phytoalexin elicitor in rice cells (ref. 7d).