2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)

X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal str...

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Detalles Bibliográficos
Autores principales: Jenkinson, Sarah. F., Crabtree, Elizabeth. V., Glawar, Andreas. F. G., Butters, Terry D., Fleet, George. W. J., Watkin, David. J.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979175/
https://www.ncbi.nlm.nih.gov/pubmed/21579195
http://dx.doi.org/10.1107/S1600536810014145
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author Jenkinson, Sarah. F.
Crabtree, Elizabeth. V.
Glawar, Andreas. F. G.
Butters, Terry D.
Fleet, George. W. J.
Watkin, David. J.
author_facet Jenkinson, Sarah. F.
Crabtree, Elizabeth. V.
Glawar, Andreas. F. G.
Butters, Terry D.
Fleet, George. W. J.
Watkin, David. J.
author_sort Jenkinson, Sarah. F.
collection PubMed
description X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, inter­molecular O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds link the mol­ecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute configuration is determined by the use of l-glucuronolactone as the starting material for the synthesis.
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spelling pubmed-29791752010-12-30 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc) Jenkinson, Sarah. F. Crabtree, Elizabeth. V. Glawar, Andreas. F. G. Butters, Terry D. Fleet, George. W. J. Watkin, David. J. Acta Crystallogr Sect E Struct Rep Online Organic Papers X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, inter­molecular O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds link the mol­ecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute configuration is determined by the use of l-glucuronolactone as the starting material for the synthesis. International Union of Crystallography 2010-04-24 /pmc/articles/PMC2979175/ /pubmed/21579195 http://dx.doi.org/10.1107/S1600536810014145 Text en © Jenkinson 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
Jenkinson, Sarah. F.
Crabtree, Elizabeth. V.
Glawar, Andreas. F. G.
Butters, Terry D.
Fleet, George. W. J.
Watkin, David. J.
2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title_full 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title_fullStr 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title_full_unstemmed 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title_short 2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)
title_sort 2-acetamido-n-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (n-benzyl-l-xylnac)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979175/
https://www.ncbi.nlm.nih.gov/pubmed/21579195
http://dx.doi.org/10.1107/S1600536810014145
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