Propargyl glycosides as stable glycosyl donors: Anomeric activation and glycoside syntheses

被引：177

作者：

Hotha, Srinivas ^{[1
]}

Kashyap, Sudhir ^{[1
]}

机构：

[1] Combi Chem Bio Resource Ctr, Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 30期

关键词：

D O I：

10.1021/ja062425c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The advantages of stable glycosyl donors for saccharide coupling are many, and we describe herein the utility of propargyl glycosides for anomeric activation and glycoside synthesis exploiting the alkynophilicity of AuCl3. Various aglycones were reacted with propargyl glycosides, resulting in the formation of an α,β-mixture of glycosides and disaccharides in good yields. Copyright © 2006 American Chemical Society.

引用

页码：9620 / 9621

页数：2

共 44 条

[21]

MCAULIFFE JC, 2000, FRONT MOL BIOL, V30, P249

[22] NORMAL-PENTENYL GLYCOSIDES PERMIT THE CHEMOSPECIFIC LIBERATION OF THE ANOMERIC CENTER [J].

MOOTOO, DR ;

DATE, V ;

FRASERREID, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2662-2663

[23] Sulfide-mediated dehydrative glycosylation [J].

Nguyen, HM ;

Chen, YN ;

Duron, SG ;

Gin, DY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (36) :8766-8772

[24] Cationic gold(I) complexes:: Highly alkynophilic catalysts for the exo- and endo-cyclization of enynes [J].

Nieto-Oberhuber, C ;

Muñoz, MP ;

Buñuel, E ;

Nevado, C ;

Cárdenas, DJ ;

Echavarren, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2402-2406

[25] ADVANCES IN SELECTIVE CHEMICAL SYNTHESES OF COMPLEX OLIGOSACCHARIDES [J].

PAULSEN, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (03) :155-173

[26] Development of an automated oligosaccharide synthesizer [J].

Plante, OJ ;

Palmacci, ER ;

Seeberger, PH .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 58, 2003, 58 :35-54

[27] Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: A synthetic route to anticancer vaccine candidates [J].

Ragupathi, G ;

Koide, F ;

Livingston, PO ;

Cho, YS ;

Endo, A ;

Wan, Q ;

Spassova, MK ;

Keding, SJ ;

Allen, J ;

Ouerfelli, O ;

Wilson, RM ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2715-2725

[28] Glycosylation and the immune system [J].

Rudd, PM ;

Elliott, T ;

Cresswell, P ;

Wilson, IA ;

Dwek, RA .

SCIENCE, 2001, 291 (5512) :2370-2376

[29] NEW METHODS FOR THE SYNTHESIS OF GLYCOSIDES AND OLIGOSACCHARIDES - ARE THERE ALTERNATIVES TO THE KOENIGS-KNORR METHOD [J].

SCHMIDT, RR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :212-235

[30] ANOMERIC-OXYGEN ACTIVATION FOR GLYCOSIDE SYNTHESIS - THE TRICHLOROACETIMIDATE METHOD [J].

SCHMIDT, RR ;

KINZY, W .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 50, 1994, 50 :21-123

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