Selective Reduction of Carbohydrate Nitroolefins
Keyword(s):
Group 5
◽
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.
2013 ◽
Vol 464-465
◽
pp. 313-321
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2019 ◽
Vol 41
(20)
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pp. 2549-2560
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Keyword(s):
2006 ◽
Vol 36
(6)
◽
pp. 765-769
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Keyword(s):