Automated electrochemical assembly of the protected potential TMG-chitotriomycin precursor based on rational optimization of the carbohydrate building block

Organic Letters
Toshiki NokamiJun-ichi Yoshida

Abstract

The anomeric arylthio group and the hydroxyl-protecting groups of thioglycosides were optimized to construct carbohydrate building blocks for automated electrochemical solution-phase synthesis of oligoglucosamines having 1,4-β-glycosidic linkages. The optimization study included density functional theory calculations, measurements of the oxidation potentials, and the trial synthesis of the chitotriose trisaccharide. The automated synthesis of the protected potential N,N,N-trimethyl-d-glucosaminylchitotriomycin precursor was accomplished by using the optimized building block.

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Citations

May 15, 2016·Molecular Aspects of Medicine·Larissa Krasnova, Chi-Huey Wong
Aug 31, 2016·The Journal of Organic Chemistry·Salvatore G PistorioAlexei V Demchenko
Dec 30, 2016·Organic Letters·Shishi LinTehshik P Yoon
Oct 26, 2016·ChemistryOpen·Rituparna Das, Balaram Mukhopadhyay
May 13, 2020·Angewandte Chemie·Miao LiuXin-Shan Ye

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