The title compound {systematic name: (2S,3R)-ethyl 3-[(3aS,4R,6S,6aS)-6-tert-butyl-dimethyl-silyl-oxy-2,2-dimethyl-per-hydro-furo[3,4-d][1,3]dioxol-4-yl]-2-nitro-3-[(S)-tetra-hydro-2H-pyran-2-yl-oxy]propanoate}, C(23)H(41)NO(10)Si, is the product of the Henry reaction of 1-O-tert-butyl-dimethyl-silyl-2,3-O-isopropyl-idene-α-d-lyxo-penta-dialdo-1,4-furan-ose with ethyl nitro-acetate and the subsequent protection of its C-5 hydr-oxy group as tetra-hydro-pyranyl, in order to avoid the retro-Henry reaction. The tetra-hydro-pyranyl group adopts a chair conformation. The absolute configuration, assumed from the synthesis, was confirmed from the diffraction data.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962108 | PMC |
http://dx.doi.org/10.1107/S1600536808021193 | DOI Listing |
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