Photoinduced Thiol-Ene Coupling as a Click Ligation Tool for Thiodisaccharide Synthesis

被引：98

作者：

Fiore, Michele ^{[1
]}

Marra, Alberto ^{[1
]}

Dondoni, Alessandro ^{[1
]}

机构：

[1] Univ Ferrara, Chim Organ Lab, Dipartmento Chim, I-44100 Ferrara, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 11期

关键词：

CHEMOENZYMATIC SYNTHESIS; UNSATURATED-COMPOUNDS; POLYETHYLENE-GLYCOL; SUPPORTED SYNTHESIS; CHEMISTRY; THIOOLIGOSACCHARIDES; THIOGLYCOSIDES; GLYCOSIDES; EFFICIENT; MIMETICS;

D O I：

10.1021/jo900514w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The high efficiency and selectivity of the thiol-ene radical reaction has been validated by the photoinduced coupling of anomeric sugar thiols with sugar alkenes to give 1,6-linked S-disaccharides in good to excellent yields (76-92%) and high diastereoselectivities (up to 99%). The reaction appears to be well-qualified as an exemplar click process.

引用

页码：4422 / 4425

页数：4

共 40 条

[1] Conformational differences between Fuc(α1-3)GlcNAc and its thioglycoside analogue [J].

Aguilera, B ;

Jiménez-Barbero, J ;

Fernández-Mayoralas, A .

CARBOHYDRATE RESEARCH, 1998, 308 (1-2) :19-27

[2] Thiooligosaccharide conjugate vaccines evoke antibodies specific for native antigens [J].

Bundle, DR ;

Rich, JR ;

Jacques, S ;

Yu, HN ;

Nitz, M ;

Ling, CC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7725-7729

[3] Use of n-pentenyl glycosides as precursors to various spacer functionalities [J].

Buskas, T ;

Söderberg, E ;

Konradsson, P ;

Fraser-Reid, B .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) :958-963

[4] The Emergence of Thiol-Ene Coupling as a Click Process for Materials and Bioorganic Chemistry [J].

Dondoni, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (47) :8995-8997

[5] Microwave irradiation for accelerating the synthesis of thioglycosides [J].

El Ashry, E. S. H. ;

Awad, L. F. ;

Hamid, H. M. Abdel ;

Atta, A. I. .

SYNTHETIC COMMUNICATIONS, 2006, 36 (19) :2769-2785

[6] Synthesis of S-linked carbohydrate analogues via a Ferrier reaction [J].

Ellis, David ;

Norman, Sarah E. ;

Osborn, Helen M. I. .

TETRAHEDRON, 2008, 64 (12) :2832-2854

[7] Probing secondary carbohydrate-protein interactions with highly dense cyclodextrin-centered heteroglycoclusters:: The heterocluster effect [J].

Gómez-García, M ;

Benito, JM ;

Rodríguez-Lucena, D ;

Yu, JX ;

Chmurski, K ;

Mellet, CO ;

Gallego, RG ;

Maestre, A ;

Defaye, J ;

Fernández, JMG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) :7970-7971

[8] Thio-click modification of poly [2-(3-butenyl)-2-oxazoline] [J].

Gress, Anja ;

Volkel, Antje ;

Schlaad, Helmut .

MACROMOLECULES, 2007, 40 (22) :7928-7933

[9] PROBLEMS AND POSSIBILITIES OF FREE-RADICAL ADDITION OF THIOLS TO UNSATURATED COMPOUNDS [J].

GRIESBAUM, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (04) :273-+

[10] Iterative synthesis of spacered glycodendrons as oligomannoside mimetics and evaluation of their antiadhesive properties [J].

Heidecke, Christoph D. ;

Lindhorst, Thisbe K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (32) :9056-9067

← 1 2 3 4 →