Selective Reduction of Carbohydrate Nitroolefins
Open Access
- 15 April 1972
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 50 (8) , 1292-1295
- https://doi.org/10.1139/v72-202
Abstract
Reduction of the four stereoisomeric methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-hex-2-enopyranosides (1–4) with sodium borohydride gave in 80–90% yield the corresponding saturated nitro glycosides that possess an equatorial nitro group (5–8). Reduction of 1–4 with zinc and acetic acid gave in similar yields the corresponding 2,3-dideoxy-3-oximino glycosides (9–12). Two of the latter were deoximated to 2,3-dideoxy-3-oxo sugar derivatives.Keywords
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