Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor

The title compound, C(13)H(24)O(7), is the product of the ketalization of methyl l-(+)-rhamnopyran­oside with 2,3-butane­dione. It crystallizes with two mol­ecules in the asymmetric unit, which are connected by O—H⋯O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyr...

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Detalles Bibliográficos
Autores principales: Tsai, Yow-Fu, Yang, Jen-Ta, Chen, Jhy-Der, Lin, Chia-Her
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961327/
https://www.ncbi.nlm.nih.gov/pubmed/21202380
http://dx.doi.org/10.1107/S1600536808008222
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author Tsai, Yow-Fu
Yang, Jen-Ta
Chen, Jhy-Der
Lin, Chia-Her
author_facet Tsai, Yow-Fu
Yang, Jen-Ta
Chen, Jhy-Der
Lin, Chia-Her
author_sort Tsai, Yow-Fu
collection PubMed
description The title compound, C(13)H(24)O(7), is the product of the ketalization of methyl l-(+)-rhamnopyran­oside with 2,3-butane­dione. It crystallizes with two mol­ecules in the asymmetric unit, which are connected by O—H⋯O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyran­oside were protected, leaving the C-2 hydroxy group free. The l-(+)-rhamnopyran­oside and 2′,3′-dimethoxy­butane-2′,3′-diyl rings adopt chair conformations and all meth­oxy groups are in axial positions. The absolute configuration was assumed from the synthesis.
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spelling pubmed-29613272010-12-30 Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor Tsai, Yow-Fu Yang, Jen-Ta Chen, Jhy-Der Lin, Chia-Her Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(24)O(7), is the product of the ketalization of methyl l-(+)-rhamnopyran­oside with 2,3-butane­dione. It crystallizes with two mol­ecules in the asymmetric unit, which are connected by O—H⋯O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyran­oside were protected, leaving the C-2 hydroxy group free. The l-(+)-rhamnopyran­oside and 2′,3′-dimethoxy­butane-2′,3′-diyl rings adopt chair conformations and all meth­oxy groups are in axial positions. The absolute configuration was assumed from the synthesis. International Union of Crystallography 2008-04-23 /pmc/articles/PMC2961327/ /pubmed/21202380 http://dx.doi.org/10.1107/S1600536808008222 Text en © Tsai 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
Tsai, Yow-Fu
Yang, Jen-Ta
Chen, Jhy-Der
Lin, Chia-Her
Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title_full Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title_fullStr Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title_full_unstemmed Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title_short Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
title_sort methyl (2′s,3′s)-3,4-o-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2961327/
https://www.ncbi.nlm.nih.gov/pubmed/21202380
http://dx.doi.org/10.1107/S1600536808008222
work_keys_str_mv AT tsaiyowfu methyl2s3s34o23dimethoxybutane23diylalrhamnopyranosideaglycosylacceptor
AT yangjenta methyl2s3s34o23dimethoxybutane23diylalrhamnopyranosideaglycosylacceptor
AT chenjhyder methyl2s3s34o23dimethoxybutane23diylalrhamnopyranosideaglycosylacceptor
AT linchiaher methyl2s3s34o23dimethoxybutane23diylalrhamnopyranosideaglycosylacceptor

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