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
References 1 Current address: Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Aoba-ku, Sendai 980-8578, Japan; e-mail: hirokazu@mail.pharm.tohoku.ac.jp.
2 Current address: Department of Chemistry, Faculty of Science Okayama University of Science, Okayama, Ridai 1-1, Okayama 700-0005, Japan; e-mail: yamada@high.ous.ac.jp.
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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).
