Saturated 2-nitrosugar derivatives (11-20 and 22) are easily synthesiz
ed by oxidation with m-CPBA of readily available corresponding 2-amino
sugars (1-10 and 21), in excellent yield. Alkyl 4,6-O-benzylidene-2-de
oxy-2-nitro-D-hexopyranoides suffer O-alkylation and O-acylation in th
e usual conditions. These 3-O-acetyl-2-nitrosugar derivatives gave the
corresponding 2-nitroalkene derivative, which reacts in situ with nuc
lephiles in high stereoselectivity.