Utilizing Reusable Catalyst Phosphotungstic Acid for the Synthesis of Thioglycoside from Per- O-acetyl Saccharides with Microwave-Assisted and De- O-acetylation with Methanol

Jyun-Siao Chen; Tai-Chung Lo; Ya-Chi Hsieh; Ching-Hsien Chen; Michelle Lin; Heng-Yan Lin; Ming-Wei Hung; Hsin-Ru Wu; Shun-Yuan Luo

doi:10.1021/acsomega.3c00362

Utilizing Reusable Catalyst Phosphotungstic Acid for the Synthesis of Thioglycoside from Per- O-acetyl Saccharides with Microwave-Assisted and De- O-acetylation with Methanol

ACS Omega. 2023 Feb 21;8(9):8885-8893. doi: 10.1021/acsomega.3c00362. eCollection 2023 Mar 7.

Authors

Jyun-Siao Chen¹, Tai-Chung Lo¹, Ya-Chi Hsieh¹, Ching-Hsien Chen¹, Michelle Lin², Heng-Yan Lin¹, Ming-Wei Hung¹, Hsin-Ru Wu³, Shun-Yuan Luo¹

Affiliations

¹ Department of Chemistry, National Chung Hsing University, Taichung 40227, Taiwan.
² Morrison Academy, Taichung 40679, Taiwan.
³ Instrumentation Center, National Tsing Hua University, MOST, Hsinchu 300044, Taiwan.

Abstract

Traditional methods for synthesizing complex oligosaccharides currently developed are not efficient, requiring a new glycosylation methodology. Herein, using phosphotungstic acid (PTA) as a catalyst has demonstrated to be a simple possibility for carbohydrate synthesis. The methodology is engineered into a PTA-catalyzed thioglycoside preparation under microwave conditions and de-O-acetylation of carbohydrates. These easier operations and convenient protocols display a wide substrate scope. Moreover, both methods can be developed into a one-pot reaction for the efficient synthesis of carbohydrate analogues.