Stereoselective Koenigs-Knorr Glycosylation Catalyzed by Urea

被引：105

作者：

Sun, Lifeng ^{[1
]}

Wu, Xiaowei ^{[1
]}

Xiong, De-Cai ^{[1
]}

Ye, Xin-Shan ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

[2] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 28期

基金：

北京市自然科学基金; 中国国家自然科学基金;

关键词：

carbohydrates; glycosylation; organocatalysis; stereoselectivity; urea; GLYCOSIDATION REACTIONS; DONORS; RECOGNITION; ACTIVATION; THIOUREA;

D O I：

10.1002/anie.201600142

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective Koenigs-Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low alpha-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl) phosphine (TTMPP).

引用

页码：8041 / 8044

页数：4

共 35 条

[1]

[Anonymous], 2013, ANGEW CHEM-GER EDIT

[2]

Balmond E. I., 2012, ANGEW CHEM, V124, P9286

[3] α-Selective Organocatalytic Synthesis of 2-Deoxygalactosides [J].

Balmond, Edward I. ;

Coe, Diane M. ;

Galan, M. Carmen ;

McGarrigle, Eoghan M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9152-9155

[4] Asymmetric Ion-Pairing Catalysis [J].

Brak, Katrien ;

Jacobsen, Eric N. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561

[5] A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor [J].

Burkart, MD ;

Zhang, ZY ;

Hung, SC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11743-11746

[6] SYNTHESIS OF THIODISACCHARIDES USING PHASE-TRANSFER CATALYSIS [J].

CHRETIEN, F ;

DICESARE, P ;

GROSS, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3297-3300

[7] Glycosylation Catalyzed by a Chiral Bronsted Acid [J].

Cox, Daniel J. ;

Smith, Martin D. ;

Fairbanks, Antony J. .

ORGANIC LETTERS, 2010, 12 (07) :1452-1455

[8]

Das S., 2015, ANGEW CHEM, V127, P12656

[9] Organocatalytic Glycosylation by Using Electron- Deficient Pyridinium Salts [J].

Das, Somnath ;

Pekel, Daniel ;

Neudoerfl, Joerg-M. ;

Berkessel, Albrecht .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12479-12483

[10] Ring-closing alkyne metathesis.: Application to the total synthesis of sophorolipid lactone [J].

Fürstner, A ;

Radkowski, K ;

Grabowski, J ;

Wirtz, C ;

Mynott, R .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8758-8762

← 1 2 3 4 →