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Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation

This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during t...

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Detalles Bibliográficos
Autores principales: Chen, Jyun-Siao, Sankar, Arumugam, Lin, Yi-Jyun, Huang, Po-Hsun, Liao, Chih-Hsiang, Wu, Shen-Shen, Wu, Hsin-Ru, Luo, Shun-Yuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073715/
https://www.ncbi.nlm.nih.gov/pubmed/35528919
http://dx.doi.org/10.1039/c9ra06170c
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author Chen, Jyun-Siao
Sankar, Arumugam
Lin, Yi-Jyun
Huang, Po-Hsun
Liao, Chih-Hsiang
Wu, Shen-Shen
Wu, Hsin-Ru
Luo, Shun-Yuan
author_facet Chen, Jyun-Siao
Sankar, Arumugam
Lin, Yi-Jyun
Huang, Po-Hsun
Liao, Chih-Hsiang
Wu, Shen-Shen
Wu, Hsin-Ru
Luo, Shun-Yuan
author_sort Chen, Jyun-Siao
collection PubMed
description This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during the synthesis of carbohydrate-based bioactive oligomers. Phosphotungstic acid's high acidity and eco-friendly character make it a tempting alternative to corrosive homogeneous acids. The various homogenous acid catalysts were replaced by the phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions.
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spelling pubmed-90737152022-05-06 Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation Chen, Jyun-Siao Sankar, Arumugam Lin, Yi-Jyun Huang, Po-Hsun Liao, Chih-Hsiang Wu, Shen-Shen Wu, Hsin-Ru Luo, Shun-Yuan RSC Adv Chemistry This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during the synthesis of carbohydrate-based bioactive oligomers. Phosphotungstic acid's high acidity and eco-friendly character make it a tempting alternative to corrosive homogeneous acids. The various homogenous acid catalysts were replaced by the phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions. The Royal Society of Chemistry 2019-10-21 /pmc/articles/PMC9073715/ /pubmed/35528919 http://dx.doi.org/10.1039/c9ra06170c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Chen, Jyun-Siao
Sankar, Arumugam
Lin, Yi-Jyun
Huang, Po-Hsun
Liao, Chih-Hsiang
Wu, Shen-Shen
Wu, Hsin-Ru
Luo, Shun-Yuan
Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title_full Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title_fullStr Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title_full_unstemmed Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title_short Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
title_sort phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073715/
https://www.ncbi.nlm.nih.gov/pubmed/35528919
http://dx.doi.org/10.1039/c9ra06170c
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