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Synthesis of aryl thioglycosides by metal-free arylation of glycosyl thiols with diaryliodonium salts under basic conditions.

作者信息

Gaurav Anand, Mandal Pintu Kumar

机构信息

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow, 226031, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow, 226031, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.

出版信息

Carbohydr Res. 2025 Jun;552:109437. doi: 10.1016/j.carres.2025.109437. Epub 2025 Feb 24.

Abstract

Herein, we demonstrate the application of unsymmetrical iodonium salts towards S-arylation of glycosyl thiols under metal-free conditions, affording a various stereoretentive thioarylglycosides in moderate to good yields. The application of an inorganic base CsCO enables the C-S bond formation under mild and experimentally simple conditions at room temperature. The proper choice of auxiliary of the unsymmetrical iodonium salt enables the access to diverse functionalized aryl moieties including biphenyl groups and its incorporation into thioarylglycosides.

摘要

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