Ethyl 1-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-5-[(2′S)-tetrahydropyran-2-yloxy]-d-glycero-α-d-manno-heptofuronate

Abstract

The title compound {systematic name: (2S,3R)-ethyl 3-[(3aS,4R,6S,6aS)-6-tert-butyldimethylsilyloxy-2,2-dimethylperhydrofuro[3,4-d][1,3]dioxol-4-yl]-2-nitro-3-[(S)-tetrahydro-2H-pyran-2-yloxy]propanoate}, C23H41NO10Si, is the product of the Henry reaction of 1-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-α-d-lyxo-pentadialdo-1,4-furanose with ethyl nitroacetate and the subsequent protection of its C-5 hydroxy group as tetrahydropyranyl, in order to avoid the retro-Henry reaction. The tetrahydropyranyl group adopts a chair conformation. The absolute configuration, assumed from the synthesis, was confirmed from the diffraction data.