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
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.
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页码:3426 / 3430
页数:5
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