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磷钨酸作为一种用于碳水化合物保护和糖基化的新型酸性催化剂。

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

作者信息

Chen Jyun-Siao, Sankar Arumugam, Lin Yi-Jyun, Huang Po-Hsun, Liao Chih-Hsiang, Wu Shen-Shen, Wu Hsin-Ru, Luo Shun-Yuan

机构信息

Department of Chemistry, National Chung Hsing University Taichung 402 Taiwan

Taichung Municipal Feng Yuan Senior High School Taichung 420 Taiwan.

出版信息

RSC Adv. 2019 Oct 21;9(58):33853-33862. doi: 10.1039/c9ra06170c. eCollection 2019 Oct 18.

DOI:10.1039/c9ra06170c
PMID:35528919
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9073715/
Abstract

This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per--acetylation, regioselective -4,6 benzylidene acetal formation, regioselective -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.

摘要

这项工作展示了磷钨酸(PTA)作为一种新型酸性催化剂在碳水化合物反应中的应用,例如全乙酰化、区域选择性4,6-亚苄基缩醛的形成、区域选择性4-开环以及糖基化反应。这些反应在基于碳水化合物的生物活性低聚物的合成过程中至关重要且显著。磷钨酸的高酸性和环境友好特性使其成为腐蚀性均相酸颇具吸引力的替代品。在不同的碳水化合物反应中,各种均相酸催化剂都被磷钨酸单独取代。由于其热稳定性好且易于操作,它可广泛用作有机反应的催化剂。在我们的工作中,反应在环境条件下顺利进行;温度从0°C到室温不等。在所有这四种反应中都获得了良好到优异的产率。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a26e/9073715/a2a815bdb856/c9ra06170c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a26e/9073715/75eae819a4b4/c9ra06170c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a26e/9073715/a2a815bdb856/c9ra06170c-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a26e/9073715/75eae819a4b4/c9ra06170c-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a26e/9073715/a2a815bdb856/c9ra06170c-f2.jpg

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2
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Chem Rev. 2018 Sep 12;118(17):8005-8024. doi: 10.1021/acs.chemrev.8b00032. Epub 2018 Aug 9.
3
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4
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5
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6
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8
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9
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J Am Chem Soc. 2016 Apr 13;138(14):4938-47. doi: 10.1021/jacs.6b01823. Epub 2016 Mar 29.
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Org Biomol Chem. 2012 Jul 28;10(28):5357-60. doi: 10.1039/c2ob25452b. Epub 2012 Jun 19.