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A new approach to the neoglycopeptides: synthesis of urea- and carbamate-tethered N-acetyl-D-glucosamine amino acid conjugates.

Ichikawa Y, Ohara F, Kotsuki H, Nakano K

Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@kochi-u.ac.jp

A novel approach to the synthesis of Fmoc-protected neoglycopeptide building blocks is described. Oxidation of N-acetyl-D-glucosamine isonitrile afforded the corresponding highly reactive glycopyranosyl isocyanate, which reacted with amino acid derivatives to furnish the corresponding urea- and carbamate-tethered Fmoc-protected N-acetyl-D-glucosamine amino acid conjugates in good yields. [reaction: see text]

Published 19 October 2006 in Org Lett, 8(22): 5009-12.
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