Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles...

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Autores principales: Ansari, Alafia A, Reddy, Y Suman, Vankar, Yashwant D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943741/
https://www.ncbi.nlm.nih.gov/pubmed/24605151
http://dx.doi.org/10.3762/bjoc.10.27
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author Ansari, Alafia A
Reddy, Y Suman
Vankar, Yashwant D
author_facet Ansari, Alafia A
Reddy, Y Suman
Vankar, Yashwant D
author_sort Ansari, Alafia A
collection PubMed
description A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles. The obtained C-allyl glycoside has been utilized for the synthesis of a orthogonally protected 2-amino-2-deoxy-C-glycoside.
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spelling pubmed-39437412014-03-06 Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside Ansari, Alafia A Reddy, Y Suman Vankar, Yashwant D Beilstein J Org Chem Full Research Paper A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected glycals and by employing several nucleophiles. The obtained C-allyl glycoside has been utilized for the synthesis of a orthogonally protected 2-amino-2-deoxy-C-glycoside. Beilstein-Institut 2014-01-30 /pmc/articles/PMC3943741/ /pubmed/24605151 http://dx.doi.org/10.3762/bjoc.10.27 Text en Copyright © 2014, Ansari 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
Ansari, Alafia A
Reddy, Y Suman
Vankar, Yashwant D
Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title_full Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title_fullStr Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title_full_unstemmed Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title_short Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside
title_sort efficient carbon-ferrier rearrangement on glycals mediated by ceric ammonium nitrate: application to the synthesis of 2-deoxy-2-amino-c-glycoside
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943741/
https://www.ncbi.nlm.nih.gov/pubmed/24605151
http://dx.doi.org/10.3762/bjoc.10.27
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