Organic letters

Enantioselective synthesis of 2-deoxy-and 2, 3-dideoxyhexoses

MH Haukaas, GA O'Doherty

Index: Haukaas, Michael H.; O'Doherty, George A. Organic Letters, 2002 , vol. 4, # 10 p. 1771 - 1774

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Citation Number: 95

Abstract

The enantioselective syntheses of C-6 O-TBS-and N-Cbz-protected 2-deoxy-and 2, 3- dideoxysugars have been achieved in 6-8 steps from furfural. A combination of chemo-, regio-, and diastereoselective oxidation and reduction reactions produced deoxysugars with various C-6 substitution. A key development of this route was the use of o- nitrobenzenesulfonylhydrazide (NBSH) as a diimide precursor. These overall procedures ...

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