Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars

The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation metho...

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Autores principales: Dangerfield, Emma Marie, Plunkett, Catherine Heather, Stocker, Bridget Louise, Timmer, Mattie Simon Maria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254907/
https://www.ncbi.nlm.nih.gov/pubmed/20032893
http://dx.doi.org/10.3390/molecules14125298
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author Dangerfield, Emma Marie
Plunkett, Catherine Heather
Stocker, Bridget Louise
Timmer, Mattie Simon Maria
author_facet Dangerfield, Emma Marie
Plunkett, Catherine Heather
Stocker, Bridget Louise
Timmer, Mattie Simon Maria
author_sort Dangerfield, Emma Marie
collection PubMed
description The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer.
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spelling pubmed-62549072018-11-30 Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars Dangerfield, Emma Marie Plunkett, Catherine Heather Stocker, Bridget Louise Timmer, Mattie Simon Maria Molecules Article The protecting-group-free asymmetric synthesis of 1,2,4-trideoxy-1,4-imino-L-xylitol is readily achieved in five steps from 2-deoxy-D-ribose and with an overall yield of 48%. Key in this synthesis is the application of our recently developed Vasella-reductive amination and carbamate annulation methodologies to the synthesis of 2-deoxy-aza-sugars. The carbamate annulation occurred with excellent yield and diastereoselectively (>20:1 d.r.), in favour of the 3,4-cis isomer. Molecular Diversity Preservation International 2009-12-16 /pmc/articles/PMC6254907/ /pubmed/20032893 http://dx.doi.org/10.3390/molecules14125298 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Dangerfield, Emma Marie
Plunkett, Catherine Heather
Stocker, Bridget Louise
Timmer, Mattie Simon Maria
Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title_full Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title_fullStr Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title_full_unstemmed Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title_short Protecting-Group-Free Synthesis of 2-Deoxy-Aza-Sugars
title_sort protecting-group-free synthesis of 2-deoxy-aza-sugars
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254907/
https://www.ncbi.nlm.nih.gov/pubmed/20032893
http://dx.doi.org/10.3390/molecules14125298
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AT stockerbridgetlouise protectinggroupfreesynthesisof2deoxyazasugars
AT timmermattiesimonmaria protectinggroupfreesynthesisof2deoxyazasugars

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