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Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently acce...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155650/ https://www.ncbi.nlm.nih.gov/pubmed/28067759 http://dx.doi.org/10.3390/molecules22010084 |
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author | Liang, Chengyuan Ju, Weihui Ding, Shunjun Sun, Han Mao, Gennian |
author_facet | Liang, Chengyuan Ju, Weihui Ding, Shunjun Sun, Han Mao, Gennian |
author_sort | Liang, Chengyuan |
collection | PubMed |
description | An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield. |
format | Online Article Text |
id | pubmed-6155650 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61556502018-11-13 Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction Liang, Chengyuan Ju, Weihui Ding, Shunjun Sun, Han Mao, Gennian Molecules Communication An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield. MDPI 2017-01-05 /pmc/articles/PMC6155650/ /pubmed/28067759 http://dx.doi.org/10.3390/molecules22010084 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Liang, Chengyuan Ju, Weihui Ding, Shunjun Sun, Han Mao, Gennian Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title_full | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title_fullStr | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title_full_unstemmed | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title_short | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
title_sort | effective synthesis of nucleosides utilizing o-acetyl-glycosyl chlorides as glycosyl donors in the absence of catalyst: mechanism revision and application to silyl-hilbert-johnson reaction |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155650/ https://www.ncbi.nlm.nih.gov/pubmed/28067759 http://dx.doi.org/10.3390/molecules22010084 |
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