Stereoselective Organocatalyzed Glycosylation of Glycosyl Trichloroacetimidate Donors: Thiouracil as Bronsted Acid Catalyst

被引：2
作者：
Tiwari, Ashwani [1 ,2 ]
Khanam, Ariza [1 ]
Lal, Mohan [1 ,2 ]
Mandal, Pintu Kumar [1 ,2 ]
机构：
[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, BS-10-1,Sect 10,Jankipuram Extens,Sitapur Rd,POB 1, Lucknow 226031, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 15期
关键词：
Organocatalyst; 2-Thiouracil; Glycosylation; O-Glycosides; alpha-Stereoselective; ACTIVATION; THIOUREAS; ACT;
D O I：
10.1002/adsc.202400067
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Herein, we report thiouracil-catalyzed alpha-selective O-glycosylations employing easily accessible glycosyl trichloroacetimidate donors without using any co-catalyst or additive. A variety of alcohol nucleophiles including saccharides, and amino acids with different protecting groups containing glycosyl trichloroacetimidate donors were successfully alpha-glycosylated using an operationally simple protocol. Moreover, mechanistic investigations suggest that thiouracil functions as Br & oslash;nsted acid/base catalyst in this glycosylation process.
引用
收藏
页码：3262 / 3268
页数：7
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