Stereoretentive Conversion to C-Glycosides from S-Glycosides via Ligand-Coupling on Sulfur(IV)

被引：0

作者：

Yang, Qian ^{[1
]}

Wen, Miao-Miao ^{[1
]}

Ruan, Yu-Jun ^{[1
]}

Wang, Xiao-Li ^{[1
]}

Zhang, Cong-Zhen ^{[1
]}

Wang, Peng-Fei ^{[1
]}

Hu, Xin-Yue ^{[1
]}

Xiao, Yu-He ^{[1
]}

Liu, Xu-Ge ^{[1
]}

机构：

[1] Henan Univ, Sch Pharm, Zhongzhou Lab Integrat Biol, State Key Lab Antiviral Drugs, Kaifeng 475004, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 04期

基金：

中国国家自然科学基金;

关键词：

SIGMA-SULFURANE; ARYL; GLYCOSYLATION; SULFOXIDES; 2-PYRIDYL; MECHANISM; ARYLATION; ARENES; ACIDS;

D O I：

10.1021/acs.orglett.4c04338

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel strategy is reported for the stereoselective synthesis of C(sp2)-C(sp3) C-glycosides, which converts heteroaryl S-glycosides into heteroaryl C-glycosides with retention of configuration through a sequential process involving oxidation and Grignard reagent attack. The new method involves the generation of a S(IV) intermediate, followed by ligand coupling of the glycosyl and heteroaryl groups to yield heteroaryl C-glycosides. The diverse heteroaryl C-glycosides were achieved with good efficiency.

引用

页码：954 / 960

页数：7

共 18 条

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