Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique

An in situ IR technique was applied in the selective synthesis of the key intermediate for rapamycin derivatives, which made the reaction endpoint easily defined. This technology solved a bothersome problem in the preparation of rapamycin derivatives, and based on this technique, the 31-OH and 42-OH...

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Autores principales: Cao, Shuang, Zhou, Xinbo, Yang, Yuanshuai, Zhong, Wu, Sun, Tiemin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271078/
https://www.ncbi.nlm.nih.gov/pubmed/24918544
http://dx.doi.org/10.3390/molecules19067770
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author Cao, Shuang
Zhou, Xinbo
Yang, Yuanshuai
Zhong, Wu
Sun, Tiemin
author_facet Cao, Shuang
Zhou, Xinbo
Yang, Yuanshuai
Zhong, Wu
Sun, Tiemin
author_sort Cao, Shuang
collection PubMed
description An in situ IR technique was applied in the selective synthesis of the key intermediate for rapamycin derivatives, which made the reaction endpoint easily defined. This technology solved a bothersome problem in the preparation of rapamycin derivatives, and based on this technique, the 31-OH and 42-OH of rapamycin were chemically modified by a series of quaternary ammonium salts to generate 11 compounds. The solubility of all these compounds was remarkably improved (25,000 times higher than that of rapamycin) and their structures were confirmed by MS, IR, 1D and 2D NMR techniques.
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spelling pubmed-62710782018-12-21 Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique Cao, Shuang Zhou, Xinbo Yang, Yuanshuai Zhong, Wu Sun, Tiemin Molecules Article An in situ IR technique was applied in the selective synthesis of the key intermediate for rapamycin derivatives, which made the reaction endpoint easily defined. This technology solved a bothersome problem in the preparation of rapamycin derivatives, and based on this technique, the 31-OH and 42-OH of rapamycin were chemically modified by a series of quaternary ammonium salts to generate 11 compounds. The solubility of all these compounds was remarkably improved (25,000 times higher than that of rapamycin) and their structures were confirmed by MS, IR, 1D and 2D NMR techniques. MDPI 2014-06-10 /pmc/articles/PMC6271078/ /pubmed/24918544 http://dx.doi.org/10.3390/molecules19067770 Text en © 2014 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 license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Cao, Shuang
Zhou, Xinbo
Yang, Yuanshuai
Zhong, Wu
Sun, Tiemin
Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title_full Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title_fullStr Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title_full_unstemmed Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title_short Selective Substitution of 31/42–OH in Rapamycin Guided by an in Situ IR Technique
title_sort selective substitution of 31/42–oh in rapamycin guided by an in situ ir technique
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271078/
https://www.ncbi.nlm.nih.gov/pubmed/24918544
http://dx.doi.org/10.3390/molecules19067770
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