Palladium-Catalyzed Cross-Coupling Reaction of Thioglycosides with (Hetero)aryl Halides

被引：54

作者：

Brachet, Etienne ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Messaoudi, Samir ^{[1
]}

Alami, Mouad ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, BioCIS UMR 8076, LabEx LERMIT,Lab Chim Therapeut,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 2-3期

关键词：

CS bond formation; (hetero)aryl halides; palladium catalysis; thioglycosides; ONE-POT SYNTHESIS; ARYL HALIDES; C-S; STEREOSELECTIVE-SYNTHESIS; ANTIMITOTIC AGENTS; REDUCING SUGARS; BOND FORMATION; EFFICIENT; THIOLS; TOSYLHYDRAZONES;

D O I：

10.1002/adsc.201200695

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

- and -thioglycosides serve as effective nucleophiles for BuchwaldHartwig cross-coupling reactions using functionalized (hetero)aryl halides. The functional group tolerance on the electrophilic partner is typically high, both benzyl and acetate protecting groups on the carbohydrate are tolerated, and anomer selectivities of thioglycosides are high in all cases studied. The efficiency of this general protocol was well demonstrated by the synthesis of 4-methyl-7-thioumbelliferyl--D-cellobioside (MUS-CB).

引用

页码：477 / 490

页数：14

共 69 条

[1] One-pot synthesis of per-O-acetylated thioglycosides from unprotected reducing sugars [J].