Copper(II) Triflate as a Mild and Efficient Catalyst for Ferrier Glycosylation: Synthesis of 2,3-Unsaturated O-Glycosides

被引：26

作者：

Srinivas, Batthula ^{[1
]}

Reddy, Thurpu Raghavender ^{[1
]}

Krishna, Palakodety Radha ^{[1
]}

Kashyap, Sudhir ^{[1
]}

机构：

[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Discovery Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNLETT | 2014年 / 25卷 / 09期

关键词：

glycosides; glycosylation; glycoconjugates; Ferrier reaction; Lewis acid; STEREOSELECTIVE-SYNTHESIS; ALLYLIC REARRANGEMENT; ASSISTED SYNTHESIS; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; GLYCALS; OLIGOSACCHARIDES; CHLORIDE; GLYCOPYRANOSIDES; ISOMERIZATION;

D O I：

10.1055/s-0033-1341232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)(2) as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.

引用

页码：1325 / 1330

页数：6

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