Ethyl 1-O-tert-butyldimethylsilyl-2,3-Oisopropylidene-5-[(20S)-tetrahydropyran2-yloxy]-D-glycero-a-D-manno-heptofuronate
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ISSN: 2056-9890
E-ISSN: 1600-5368
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International Union of Crystallography
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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-butyldimethylsilyl2,3-O-isopropylidene--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
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Soengas, Raquel G. ; Valencia, Laura ; Estévez, Juan C. ; Estévez, Ramón J. (2008). Ethyl 1-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-5-[(2′S)-tetrahydropyran-2-yloxy]-D-glycero-α-D-manno-heptofuronate. " Acta Crystallographica Section E", E64, o1478
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https://doi.org/10.1107/S1600536808021193Sponsors
We gratefully acknowledge the Spanish Education Secretary and the Xunta de Galicia for financial support and the Spanish Education Secretary for a grant to RGS
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© 2008 by the authors. Licensee International Union of Crystallography. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license