Copper(II) Triflate: A Versatile Catalyst for the One-Pot Preparation of Orthogonally Protected Glycosides

被引：44

作者：

Anh-Tuan Tran ^{[1
]}

Jones, Rachel A. ^{[1
]}

Pastor, Julien ^{[1
]}

Boisson, Julien ^{[1
]}

Smith, Nichola ^{[2
]}

Galan, M. Carmen ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] Novartis Horsham Res Ctr, Novartis Inst Biomol Res, Horsham RH12 5AB, W Sussex, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 14-15期

基金：

英国工程与自然科学研究理事会;

关键词：

carbohydrates; catalysis; copper(II) triflate; oligosaccharide synthesis; one-pot procedure; OLIGOSACCHARIDE SYNTHESIS; REGIOSELECTIVE PROTECTION; ACETALATION-ACETYLATION; SUGAR-DERIVATIVES; ORGANIC-SYNTHESIS; EFFICIENT; GLYCOSYLATION; MONOSACCHARIDES; THIOGLYCOSIDES; GLYCOPROTEIN;

D O I：

10.1002/adsc.201100228

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one-pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes.

引用

页码：2593 / 2598

页数：6