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

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-02-24 DOI:10.1016/j.carres.2025.109437

Anand Gaurav , Pintu Kumar Mandal

引用次数: 0

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 Cs₂CO₃ 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.

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糖基硫醇与二芳基碘鎓盐在碱性条件下无金属芳化合成芳基硫甙

在此，我们展示了不对称碘盐在无金属条件下对糖基硫醇s -芳基化的应用，以中等到良好的收率提供了各种立体保持的硫基糖苷。应用无机碱Cs2CO3可以在温和且实验简单的室温条件下形成C-S键。不对称碘盐助剂的适当选择可以获得包括联苯在内的各种功能化芳基基团，并将其并入硫芳基苷中。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".