Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block

作者：Nokami Toshiki^*; Isoda Yuta; Sasaki Norihiko; Takaiso Aki; Hayase Shuichi; Itoh Toshiyuki; Hayashi Ryutaro; Shimizu Akihiro; Yoshida Jun ichi

来源：Organic Letters, 2015, 17(6): 1525-1528.

DOI：10.1021/acs.orglett.5b00406

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-beta-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.

• 出版日期2015-3-20