Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitor...

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Detalles Bibliográficos
Autores principales: Bella, Maroš, Koóš, Miroslav, Lin, Chun-Hung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578356/
https://www.ncbi.nlm.nih.gov/pubmed/26425214
http://dx.doi.org/10.3762/bjoc.11.170
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author Bella, Maroš
Koóš, Miroslav
Lin, Chun-Hung
author_facet Bella, Maroš
Koóš, Miroslav
Lin, Chun-Hung
author_sort Bella, Maroš
collection PubMed
description A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF(3)·OEt(2), 2-methyloxazoline derivatives 13 and 14 were isolated.
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spelling pubmed-45783562015-09-30 Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives Bella, Maroš Koóš, Miroslav Lin, Chun-Hung Beilstein J Org Chem Full Research Paper A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF(3)·OEt(2), 2-methyloxazoline derivatives 13 and 14 were isolated. Beilstein-Institut 2015-09-04 /pmc/articles/PMC4578356/ /pubmed/26425214 http://dx.doi.org/10.3762/bjoc.11.170 Text en Copyright © 2015, Bella et al. 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
Bella, Maroš
Koóš, Miroslav
Lin, Chun-Hung
Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_full Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_fullStr Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_full_unstemmed Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_short Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_sort towards inhibitors of glycosyltransferases: a novel approach to the synthesis of 3-acetamido-3-deoxy-d-psicofuranose derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4578356/
https://www.ncbi.nlm.nih.gov/pubmed/26425214
http://dx.doi.org/10.3762/bjoc.11.170
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