Synthesis 2013; 45(4): 471-478
DOI: 10.1055/s-0032-1318106
paper
© Georg Thieme Verlag Stuttgart · New York

Water-Dependent Reduction of Carbohydrate Azides by Dithiothreitol

Bozhena S. Komarova
Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7(499)1358784   Email: nen@ioc.ac.ru
,
Sofia S. Maryasina
Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7(499)1358784   Email: nen@ioc.ac.ru
,
Yury E. Tsvetkov
Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7(499)1358784   Email: nen@ioc.ac.ru
,
Nikolay E. Nifantiev*
Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7(499)1358784   Email: nen@ioc.ac.ru
› Author Affiliations
Further Information

Publication History

Received: 01 November 2012

Accepted after revision: 21 December 2012

Publication Date:
18 January 2013 (online)


Dedicated to Professor Genrikh A. Tolstikov on the occasion of his 80th birthday

Abstract

Dithiothreitol efficiently reduces carbohydrate azides in aqueous acetonitrile to give good-to-excellent yields of the corresponding amines or, after N-acetylation, acetamides. This reduction can proceed in either the presence or the absence of a base.

Supporting Information

 
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