Ethyl 1-O-tert-butyl-dimethyl-silyl-2,3-O-isopropyl-idene-5-[(2'S)-tetra-hydro-pyran-2-yl-oxy]-d-glycero-?-d-manno-hepto-furonate.

ABSTRACT: 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-?-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.

SUBMITTER: Soengas RG 

PROVIDER: S-EPMC2962108 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature