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

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

Jyun-Siao Chen  1 , Arumugam Sankar  1 , Yi-Jyun Lin  1 , Po-Hsun Huang  1 , Chih-Hsiang Liao  2 , Shen-Shen Wu  3 , Hsin-Ru Wu  4 , Shun-Yuan Luo  1
Affiliations

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

Jyun-Siao Chen et al. RSC Adv. .

Abstract

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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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Reactions of carbohydrates with phosphotungstic acid as the catalyst.
Fig. 2
Fig. 2. Structures of the disaccharide of chitosan 7, lipid A 8 and hyaluronic acid 9.
See this image and copyright information in PMC

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