Authors
Citation
Jm. Vegaperez et al., A FACILE SYNTHESIS OF SATURATED 2-NITROSUGAR DERIVATIVES, Journal of organic chemistry, 62(19), 1997, pp. 6608-6611
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00223263
Volume
62
Issue
19
Year of publication
1997
Pages
6608 - 6611
Database
ISI
SICI code
0022-3263(1997)62:19<6608:AFSOS2>2.0.ZU;2-T
Abstract
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.