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

共 51 条

[1]

Boltje TJ, 2009, NAT CHEM, V1, P611, DOI [10.1038/NCHEM.399, 10.1038/nchem.399]

[2] Iron(III) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides [J].

Bourdreux, Yann ;

Lemetais, Aurelie ;

Urban, Dominique ;

Beau, Jean-Marie .

CHEMICAL COMMUNICATIONS, 2011, 47 (07) :2146-2148

[3] Regioselective One-Pot Protection of D-Glucosamine [J].

Chang, Ken-Lien ;

Zulueta, Medel Manuel L. ;

Lu, Xin-An ;

Zhong, Yong-Qing ;

Hung, Shang-Cheng .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21) :7424-7427

[4] Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate [J].

Chen, CT ;

Weng, SS ;

Kao, JQ ;

Lin, CC ;

Jan, MD .

ORGANIC LETTERS, 2005, 7 (15) :3343-3346

[5] REGIOSELECTIVE MANIPULATION OF HYDROXYL-GROUPS VIA ORGANOTIN DERIVATIVES [J].

DAVID, S ;

HANESSIAN, S .

TETRAHEDRON, 1985, 41 (04) :643-663

[6] Stereoselective synthesis of muco-quercitol, (+)-gala-quercitol and 5-amino-5-deoxy-D-vibo-quercitol from D-mannitol [J].

Doddi, Venkata Ramana ;

Kumar, Amit ;

Vankar, Yashwant D. .

TETRAHEDRON, 2008, 64 (38) :9117-9122

[7] Tuning glycoside reactivity:: New tool for efficient oligosaccharide synthesis [J].

Douglas, NL ;

Ley, SV ;

Lücking, U ;

Warriner, SL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (01) :51-65

[8] Recent Trends in Regioselective Protection and Deprotection of Monosaccharides [J].

Filice, Marco ;

Guisan, Jose M. ;

Palomo, Jose M. .

CURRENT ORGANIC CHEMISTRY, 2010, 14 (06) :516-532

[9]

Francais A., 2007, Angewandte Chemie, V119, P8816

[10] Tandem catalysis for a one-pot regioselective protection of carbohydrates:: The example of glucose [J].

Francais, Antoine ;

Urban, Dominique ;

Beau, Jean-Marie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (45) :8662-8665

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