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

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}, C(23)H(41)NO(10)Si, is the product of the Henry reaction of 1-O-tert-butyl­dimethyl­sily...

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Detalles Bibliográficos
Autores principales: Soengas, Raquel G., Valencia, Laura, Estévez, Juan C., Estévez, Ramón J.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962108/
https://www.ncbi.nlm.nih.gov/pubmed/21203190
http://dx.doi.org/10.1107/S1600536808021193
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author Soengas, Raquel G.
Valencia, Laura
Estévez, Juan C.
Estévez, Ramón J.
author_facet Soengas, Raquel G.
Valencia, Laura
Estévez, Juan C.
Estévez, Ramón J.
author_sort Soengas, Raquel G.
collection PubMed
description 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}, C(23)H(41)NO(10)Si, 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.
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spelling pubmed-29621082010-12-30 Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate Soengas, Raquel G. Valencia, Laura Estévez, Juan C. Estévez, Ramón J. Acta Crystallogr Sect E Struct Rep Online Organic Papers 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}, C(23)H(41)NO(10)Si, 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. International Union of Crystallography 2008-07-12 /pmc/articles/PMC2962108/ /pubmed/21203190 http://dx.doi.org/10.1107/S1600536808021193 Text en © Soengas et al. 2008 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Soengas, Raquel G.
Valencia, Laura
Estévez, Juan C.
Estévez, Ramón J.
Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title_full Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title_fullStr Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title_full_unstemmed Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title_short Ethyl 1-O-tert-butyl­dimethyl­silyl-2,3-O-isopropyl­idene-5-[(2′S)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
title_sort ethyl 1-o-tert-butyl­dimethyl­silyl-2,3-o-isopropyl­idene-5-[(2′s)-tetra­hydro­pyran-2-yl­oxy]-d-glycero-α-d-manno-hepto­furonate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2962108/
https://www.ncbi.nlm.nih.gov/pubmed/21203190
http://dx.doi.org/10.1107/S1600536808021193
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