Behaviour of the primary nitro group under denitration conditions

Article abstract of DOI:10.1080/07328300008544067

Treatment of per-O-acetylated or acetalated glycosylnitromethanes derived from the common hexoses and pentoses with tributyltin hydride and a catalytic amount of a radical initiator [1,1′-azobis(cyclohexanecarbonitrile)] in refluxing benzene easily afforded the corresponding glycosylmethanal oximes in 84-97% yields. Per-O-acetylated C-β-glycopyranosylmethanal oximes were employed for synthesis of versatile C-β-glycopyranosyl cyanides of the β-D-gluco, β-D-manno, β-D-galacto, β-D-xylo, and β-L-rhamno configurations.

Full text of DOI:10.1080/07328300008544067

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Journal of Carbohydrate Chemistry
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Behaviour of the Primary Nitro
Group Under Denitration Conditions
Duy-Phong Pham-Huu , Mária Petrušová , James N. BeMiller &
Ladislav Petruš
a
Institute of Chemistry, Slovak Academy of Sciences, 84238
Bratislava, Slovakia
b
Institute of Chemistry, Slovak Academy of Sciences, 84238
Bratislava, Slovakia
c
The Whistler Center for Carbohydrate Research, Purdue
University, West Lafayette, IN 47907-1160, USA
d
Institute of Chemistry, Slovak Academy of Sciences, 84238
Bratislava, Slovakia
Published online: 27 Feb 2008.
To cite this article: Duy-Phong Pham-Huu , Mária Petrušová , James N. BeMiller & Ladislav
Petruš (2000) Behaviour of the Primary Nitro Group Under Denitration Conditions, Journal of
Carbohydrate Chemistry, 19:1, 93-110, DOI: 10.1080/07328300008544067
To link to this article: http://dx.doi.org/10.1080/07328300008544067
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