Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of β-d-glycosylamines

Sridhar, Perali Ramu ; Prabhu, Kandikere Ramaiah ; Chandrasekaran, Srinivasan (2003) Selective reduction of anomeric azides to amines with tetrathiomolybdate: synthesis of β-d-glycosylamines Journal of Organic Chemistry, 68 (13). pp. 5261-5264. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0266947

Related URL: http://dx.doi.org/10.1021/jo0266947

Abstract

A number of β-d-glycosyl azide derivatives undergo reduction on treatment with tetrathiomolybdate to produce the corresponding β-d-glycosylamines exclusively without anomerization under very mild and neutral reaction conditions. Acetyl, allyl, benzoyl, and benzyl protective groups are left untouched under the reaction conditions. An exclusive selectivity in the reduction of anomeric azides is observed, while the C-2 and C-6 azides are left untouched.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:7193
Deposited On:25 Oct 2010 12:18
Last Modified:01 Feb 2011 10:50

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