ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides

被引：49

作者：

Gorityala, Bala Kishan ^{[1
]}

Lorpitthaya, Rujee ^{[1
]}

Bai, Yaguang ^{[1
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

TETRAHEDRON | 2009年 / 65卷 / 29-30期

关键词：

FACILE SYNTHESIS; ALLYLIC-REARRANGEMENT; NATURAL-PRODUCTS; PENTENYL ESTERS; GLYCOSIDATION; GLYCALS; GLYCOSYLATION; MILD;

D O I：

10.1016/j.tet.2009.04.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated-O-glycosides with high alpha-selectivity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5844 / 5848

页数：5

共 40 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] DENOVA SYNTHESIS OF CARBOHYDRATES AND RELATED NATURAL-PRODUCTS .6. SYNTHESIS AND GLYCOSIDATION REACTIONS OF ACETYLATED RACEMIC PSEUDOGLYCALS [J].

ANGERBAUER, R ;

SCHMIDT, RR .

CARBOHYDRATE RESEARCH, 1981, 89 (02) :193-201

[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] 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

[8]

BRITO TMB, 1999, J CARBOHYD CHEM, V18, P609

[9] Microwave-induced synthesis of 2,3-unsaturated O-glycosides under solvent-free conditions [J].

de Oliveira, RN ;

de Freitas, JR ;

Srivastava, RM .

TETRAHEDRON LETTERS, 2002, 43 (12) :2141-2143

[10] Microwave-enhanced Ferrier reaction:: A facile synthesis of 2,3-unsaturated-O-glycosides under solvent-free conditions [J].

Du, Wenting ;

Hu, Yongzhou .

SYNTHETIC COMMUNICATIONS, 2006, 36 (14) :2035-2046

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