The 2-(allyloxy) phenyl acetyl ester as a new relay protecting group for oligosaccharide synthesis

被引：17

作者：

Arranz, E ^{[1
]}

Boons, GJ ^{[1
]}

机构：

[1] Univ Georgia, Complex Carbohydrate Res Ctr, Athens, GA 30602 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(01)01303-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-(allyloxy) phenyl acetyl group can be removed by a relay approach using Pd(PPh3)(4) in combination with proton sponge, conditions that do not affect acetyl, benzoyl and levulinoyl esters. On the other hand, the acetyl and levulinoyl ester could be cleaved without removal of the 2-(allyloxy) phenyl acetyl group. The new protecting group is compatible with glycosylations and can perform efficiently neighboring group participation leading to the exclusive formation of 1,2-trans glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6469 / 6471

页数：3

共 20 条

[1] Combinatorial chemistry for the synthesis of carbohydrate libraries [J].

Arya, P ;

Ben, RN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (12) :1280-1282

[2] SYNTHESIS OF 6-DEOXY-D-MANNO-HEPTOSE [J].

BOREN, HB ;

EKLIND, K ;

GAREGG, PJ ;

LINDBERG, B ;

PILOTTI, A .

ACTA CHEMICA SCANDINAVICA, 1972, 26 (10) :4143-4146

[3] STUDIES OF TRIFLUOROACETIC ACID .7. THE SYNTHESIS OF 2-BENZOYL 4-6-BENZYLIDENE METHYL-ALPHA-D-GLUCOPYRANOSIDE AND ITS CONVERSION INTO THE ISOMERIC 3-BENZOATE BY AN ACYL MIGRATION [J].

BOURNE, EJ ;

HUGGARD, AJ ;

TATLOW, JC .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAR) :735-741

[4] Chemoselective protection of carboxylic acid as methyl ester: A practical alternative to diazomethane protocol [J].

Chakraborti, AK ;

Basak, A ;

Grover, V .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :8014-8017

[5] Guanidine/guanidinium nitrate; A mild and selective O-deacetylation reagent that leaves the N-Troc group intact. [J].

Ellervik, U ;

Magnusson, G .

TETRAHEDRON LETTERS, 1997, 38 (09) :1627-1628

[6] PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE-TRANSFER-CATALYZED BENZOYLATION AND BENZYLATION [J].

GAREGG, PJ ;

KVARNSTROM, I ;

NIKLASSON, A ;

NIKLASSON, G ;

SVENSSON, SCT .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (07) :933-953

[7] Recent progress in polymer-supported synthesis of oligosaccharides and carbohydrate libraries [J].

Haase, WC ;

Seeberger, PH .

CURRENT ORGANIC CHEMISTRY, 2000, 4 (05) :481-511

[8] ONE-STAGE GLYCOSYLATION USING PROTECTED GLYCOSE - THE SYNTHESIS OF O-BETA-D-GLUCOPYRANOSYL-(1-]3)-O-[BETA-D-GLUCOPYRANOSYL-(1-]6)]-D-GLUCOPYRANOSE [J].

KOTO, S ;

INADA, S ;

YOSHIDA, T ;

TOYAMA, M ;

ZEN, S .

CANADIAN JOURNAL OF CHEMISTRY, 1981, 59 (02) :255-259

[9]

SCHWEIZER F, 1909, CURR OPIN CHEM BIOL, V2, P291

[10]

St Hilaire PM, 2000, ANGEW CHEM INT EDIT, V39, P1162, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1162::AID-ANIE1162>3.0.CO

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