Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

被引：29
|
作者：
Li, Jiagen [1 ]
Wang, Ming [1 ]
Jiang, Xuefeng [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 23期
关键词：
RESEMBLE GRANDFATHER GLUCOSE; 2,3-UNSATURATED SUGARS; C-ARYL; CHEMICAL-SYNTHESIS; GLYCOSIDES; EFFICIENT; PROGENY; FACILE; GLYCOPEPTIDES; CARBOHYDRATE;
D O I：
10.1021/acs.orglett.1c03302
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on alpha-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl alpha-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of alpha-sulfoxide-rhamnoside and alpha-sulfoxide-glucoside, respectively.
引用
收藏
页码：9053 / 9057
页数：5
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