Enantioselective Synthesis of 2-Deoxy- and 2,3-Dideoxyhexoses
- 23 April 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (10) , 1771-1774
- https://doi.org/10.1021/ol025844x
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 allow for the synthesis of eight deoxysugars in either enantiomeric form.Keywords
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