Selective Reduction of Carbohydrate Nitroolefins

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.