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International Union of Crystallography, Acta Crystallographica Section E: Structure Reports Online, 8(64), p. o1478-o1478, 2008

DOI: 10.1107/s1600536808021193

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

Journal article published in 2008 by Raquel G. Soengas ORCID, Laura Valencia, Juan C. Estévez, Ramón J. Estévez ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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-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.