6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose

The title compound, C(19)H(30)O(9), was prepared by substitution at the C6 position in 1,2;3,4-di-O-isopropyl­idene-6-O-trifluoro­methane­sulfonyl-d-galactose using sodium eth­oxy­malonate in dimethyl­formamide. The conformation is skew-boat (0) S (2), slightly distorted towards boat B (2,5). The in...

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Detalles Bibliográficos
Autores principales: Doboszewski, Bogdan, da Silva, Paulo R., Nazarenko, Alexander Y., Nemykin, Victor N.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011695/
https://www.ncbi.nlm.nih.gov/pubmed/21589509
http://dx.doi.org/10.1107/S1600536810046921
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author Doboszewski, Bogdan
da Silva, Paulo R.
Nazarenko, Alexander Y.
Nemykin, Victor N.
author_facet Doboszewski, Bogdan
da Silva, Paulo R.
Nazarenko, Alexander Y.
Nemykin, Victor N.
author_sort Doboszewski, Bogdan
collection PubMed
description The title compound, C(19)H(30)O(9), was prepared by substitution at the C6 position in 1,2;3,4-di-O-isopropyl­idene-6-O-trifluoro­methane­sulfonyl-d-galactose using sodium eth­oxy­malonate in dimethyl­formamide. The conformation is skew-boat (0) S (2), slightly distorted towards boat B (2,5). The inflexible pyran­ose structure makes the title compound a suitable inter­mediate for further synthetic work by keeping stereogenic carbon atoms safe from inversion. Several short intra­molecular C—H⋯ O contacts may stabilize the conformation of the mol­ecule. Inter­molecular C—H⋯O inter­actions also occur.
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spelling pubmed-30116952010-12-30 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose Doboszewski, Bogdan da Silva, Paulo R. Nazarenko, Alexander Y. Nemykin, Victor N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(30)O(9), was prepared by substitution at the C6 position in 1,2;3,4-di-O-isopropyl­idene-6-O-trifluoro­methane­sulfonyl-d-galactose using sodium eth­oxy­malonate in dimethyl­formamide. The conformation is skew-boat (0) S (2), slightly distorted towards boat B (2,5). The inflexible pyran­ose structure makes the title compound a suitable inter­mediate for further synthetic work by keeping stereogenic carbon atoms safe from inversion. Several short intra­molecular C—H⋯ O contacts may stabilize the conformation of the mol­ecule. Inter­molecular C—H⋯O inter­actions also occur. International Union of Crystallography 2010-11-17 /pmc/articles/PMC3011695/ /pubmed/21589509 http://dx.doi.org/10.1107/S1600536810046921 Text en © Doboszewski et al. 2010 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
Doboszewski, Bogdan
da Silva, Paulo R.
Nazarenko, Alexander Y.
Nemykin, Victor N.
6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title_full 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title_fullStr 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title_full_unstemmed 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title_short 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl­idene-d-galacto­pyran­ose
title_sort 6-[bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-o-isopropyl­idene-d-galacto­pyran­ose
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011695/
https://www.ncbi.nlm.nih.gov/pubmed/21589509
http://dx.doi.org/10.1107/S1600536810046921
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AT nemykinvictorn 6bisethoxycarbonylmethyl6deoxy1234dioisopropylidenedgalactopyranose

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