Regioselective direct sulfenylation of glycals using arylsulfonyl chlorides in the presence of triphenylphosphine: access to C2-thioaryl glycosides

被引：9

作者：

Kumar, Harikesh ^{[1
]}

Dubey, Atul ^{[1
]}

Prajapati, Gurudayal ^{[2
]}

Kant, Ruchir ^{[3
]}

Ampapathi, Ravi S. ^{[2
,4
]}

Mandal, Pintu Kumar ^{[1
,4
]}

机构：

[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India

[2] CSIR Cent Drug Res Inst, NMR Ctr, SAIF, Lucknow 226031, Uttar Pradesh, India

[3] CSIR Cent Drug Res Inst, Mol & Struct Biol Div, Lucknow 226031, Uttar Pradesh, India

[4] Acad Sci & Innovat Res, Ghaziabad 201002, India

来源：

NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 07期

关键词：

BETA-C-GLYCOSIDES; BOND FORMATION; CATALYZED SYNTHESIS; THIO-SUGARS; H BOND; INDOLES; THIOGLYCOSIDES; ENERGY; THIOOLIGOSACCHARIDES; 3-SULFENYLATION;

D O I：

10.1039/d1nj05228d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct triphenylphosphine-mediated regioselective sulfenylation of glycals by using various cheap and easily available aryl sulfonyl chlorides as a sulfur source to generate different C2-S-aryl-glycosides was developed. Notably, the features of this protocol offer a milder and easier operational procedure, and broad substrate scope with complete regioselectivity at C-2. Experiments and DFT calculations supported the proposed mechanism and regioselectivity for the formation of C2-S-aryl-glycosides.

引用

页码：3426 / 3430

页数：5