A Facile Synthesis of Saturated 2-Nitrosugar Derivatives

Saturated 2-nitrosugar derivatives (11−20 and 22) are easily synthesized by oxidation with m-CPBA of readily available corresponding 2-aminosugars (1−10 and 21), in excellent yield. Alkyl 4,6-O-benzylidene-2-deoxy-2-nitro-d-hexopyranosides suffer O-alkylation and O-acylation in the usual conditions....

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Published inJournal of organic chemistry Vol. 62; no. 19; pp. 6608 - 6611
Main Authors Vega-Pérez, José M, Candela, José I, Iglesias-Guerra, Fernando
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOPHILIC-ADDITION REACTIONS
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Summary:Saturated 2-nitrosugar derivatives (11−20 and 22) are easily synthesized by oxidation with m-CPBA of readily available corresponding 2-aminosugars (1−10 and 21), in excellent yield. Alkyl 4,6-O-benzylidene-2-deoxy-2-nitro-d-hexopyranosides suffer O-alkylation and O-acylation in the usual conditions. These 3-O-acetyl-2-nitrosugar derivatives gave the corresponding 2-nitroalkene derivative, which reacts in situ with nuclephiles in high stereoselectivity.
Bibliography:istex:CB39D266C22361C0CC94FEB089F035B380EBAEB0
Abstract published in Advance ACS Abstracts, September 1, 1997.
ark:/67375/TPS-BJ0K1VKM-C
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9707139