Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9

A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic g...

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Autores principales: Santra, Abhishek, Misra, Anup Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182426/
https://www.ncbi.nlm.nih.gov/pubmed/21977201
http://dx.doi.org/10.3762/bjoc.7.137
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author Santra, Abhishek
Misra, Anup Kumar
author_facet Santra, Abhishek
Misra, Anup Kumar
author_sort Santra, Abhishek
collection PubMed
description A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield.
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spelling pubmed-31824262011-10-05 Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 Santra, Abhishek Misra, Anup Kumar Beilstein J Org Chem Full Research Paper A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield. Beilstein-Institut 2011-08-29 /pmc/articles/PMC3182426/ /pubmed/21977201 http://dx.doi.org/10.3762/bjoc.7.137 Text en Copyright © 2011, Santra and Misra https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Santra, Abhishek
Misra, Anup Kumar
Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title_full Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title_fullStr Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title_full_unstemmed Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title_short Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
title_sort convergent synthesis of the tetrasaccharide repeating unit of the o-antigen of shigella boydii type 9
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182426/
https://www.ncbi.nlm.nih.gov/pubmed/21977201
http://dx.doi.org/10.3762/bjoc.7.137
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