Scope of AuCl3 in the activation of per-O-acetylglycals

被引：58

作者：

Balamurugan, Rengarajan ^{[1
]}

Koppolu, Srinivasa Rao ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON | 2009年 / 65卷 / 39期

关键词：

GOLD-CATALYZED REACTIONS; STEREOSELECTIVE-SYNTHESIS; FERRIER REARRANGEMENT; ALLYLIC-REARRANGEMENT; FACILE SYNTHESIS; GLYCOSYLATION; GLYCALS; GLYCOSIDATION; ALKYNOPHILICITY; TRICHLORIDE;

D O I：

10.1016/j.tet.2009.07.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make beta-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：8139 / 8142

页数：4

相关论文

共 46 条

[1] Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals [J].

Agarwal, A ;

Rani, S ;

Vankar, YD .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :6137-6140

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3] Lithium tetrafluoborate catalyzed Ferrier rearrangement - Facile synthesis of alkyl 2,3-unsaturated glycopyranosides [J].

Babu, BS ;

Balasubramanian, KK .

SYNTHETIC COMMUNICATIONS, 1999, 29 (24) :4299-4305

[4]

Babu BS, 2000, TETRAHEDRON LETT, V41, P1271

[5] ZnCl2-catalyzed Ferrier reaction;: synthesis of 2,3-unsaturated 1-O-glucopyranosides of allylic, benzylic and tertiary alcohols [J].

Bettadaiah, BK ;

Srinivas, P .

TETRAHEDRON LETTERS, 2003, 44 (39) :7257-7259

[6] ALLYLIC REARRANGEMENT OF 6-DEOXYGLYCALS HAVING PRACTICAL UTILITY [J].

BHATE, P ;

HORTON, D ;

PRIEBE, W .

CARBOHYDRATE RESEARCH, 1985, 144 (02) :331-337

[7] HYDROGENOLYSIS OF CARBOHYDRATE ACETALS KETALS AND CYCLIC ORTHOESTERS WITH LITHIUM ALUMINIUM YDRIDE - ALUMINIUM TRICHLORIDE [J].

BHATTACH.SS ;

GORIN, PAJ .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (07) :1195-&

[8] Synthesis of 4-(4,6-di-0-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)pyrazoles from 3,4,6-tri-O-acetyl-D-glucal [J].

Borrachero-Moya, P ;

Cabrera-Escribano, F ;

Gómez-Guillén, M ;

Paredes-León, MDR .

CARBOHYDRATE RESEARCH, 1998, 308 (1-2) :181-190

[9] Synthesis of C-glycosyl amino acids:: scope and limitations of the tandem Tebbe/Claisen approach [J].

Chambers, DJ ;

Evans, GR ;

Fairbanks, AJ .

TETRAHEDRON-ASYMMETRY, 2005, 16 (01) :45-55

[10] Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence [J].

Danishefsky, SJ ;

Bilodeau, MT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1380-1419

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