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Synlett 1998; 1998(12): 1319-1320
DOI: 10.1055/s-1998-1950
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One-Step Conversion of C-Glycopyranosylnitromethanes to the Corresponding Methanal Oximes

Duy-Phong Pham-Huu* , Mária Petrušová, James N. BeMiller, Ladislav Petruš
  • *Institute of Chemistry, Slovak Academy of Sciences, 84238 Bratislava, Slovakia; Fax + 421-7-37-55 65; E-mail: chemlpet@savba.sk
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Publication Date:
31 December 2000 (online)

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A novel method for preparation of C-glycopyranosylmethanal oximes is described. Treatment of per-O-acetylated C-glycopyranosylnitromethanes of the β-D-gluco, β-D-manno, β-D-galacto, β-D-xylo, and β-L-rhamno configurations with tributyltin hydride and a catalytic amount of 1,1′-azobis(cyclohexanecarbonitrile) afforded the corresponding methanal oximes in isolated yields of 84-97%.

C-glycosylnitromethanes - oximes - reduction - Bu3SnH - denitration