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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
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Original Articles

Synthesis of Ureido-Linked Glycosylated Amino Acids from Nα-Fmoc-Asp/Glu-5-oxazolidinones and Their Application to Neoglycopeptide Synthesis

, , &
Pages 3640-3654 | Received 04 Feb 2008, Published online: 14 Oct 2008
 

Abstract

A simple route for the synthesis of ureido-linked glycosylated amino acids has been described. The key step involves the reaction of isocyanates derived from N α-Fmoc-Asp/Glu-5-oxazolidinones 1 with glycosyl amines followed by hydrolysis. The resulting ureido-linked glycosylated amino acids have been incorporated into peptides. The overall procedure is simple, high-yielding, and involves fewer steps.

ACKNOWLEDGMENTS

Authors are grateful to the Department of Science and Technology, Government of India, for financial support. R. V. is grateful to the CSIR for the award of a fellowship.

Notes

a HRMS.

b ES-MS.

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