AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr(3) in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars....

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Autores principales: Rajput, Jayashree, Hotha, Srinivas, Vangala, Madhuri
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870170/
https://www.ncbi.nlm.nih.gov/pubmed/29623131
http://dx.doi.org/10.3762/bjoc.14.56
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author Rajput, Jayashree
Hotha, Srinivas
Vangala, Madhuri
author_facet Rajput, Jayashree
Hotha, Srinivas
Vangala, Madhuri
author_sort Rajput, Jayashree
collection PubMed
description Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr(3) in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C.
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spelling pubmed-58701702018-04-05 AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars Rajput, Jayashree Hotha, Srinivas Vangala, Madhuri Beilstein J Org Chem Full Research Paper Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr(3) in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C. Beilstein-Institut 2018-03-22 /pmc/articles/PMC5870170/ /pubmed/29623131 http://dx.doi.org/10.3762/bjoc.14.56 Text en Copyright © 2018, Rajput et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Rajput, Jayashree
Hotha, Srinivas
Vangala, Madhuri
AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title_full AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title_fullStr AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title_full_unstemmed AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title_short AuBr(3)-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
title_sort aubr(3)-catalyzed azidation of per-o-acetylated and per-o-benzoylated sugars
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870170/
https://www.ncbi.nlm.nih.gov/pubmed/29623131
http://dx.doi.org/10.3762/bjoc.14.56
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