4.8 Article

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

Journal

ORGANIC LETTERS
Volume 17, Issue 6, Pages 1525-1528

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00406

Keywords

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Funding

  1. MEXT, Japan [2105]
  2. JSPS [21410115]
  3. UBE Foundation
  4. Electric Technology Research Foundation of Chugoku
  5. Grants-in-Aid for Scientific Research [26241030, 25410200, 25410115] Funding Source: KAKEN

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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.

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