Anchimeric assistance by the anomeric phenylthio group in the nucleophilic substitution of a 6-O-trifluoromethanesulfonyl-β-D-galactopyranoside

被引：7

作者：

Compain-Batissou, M ^{[1
]}

Mesrari, L ^{[1
]}

Anker, D ^{[1
]}

Doutheau, A ^{[1
]}

机构：

[1] Inst Natl Sci Appl, EA 1844, Chim Organ Lab, F-69621 Villeurbanne, France

来源：

CARBOHYDRATE RESEARCH | 1999年 / 316卷 / 1-4期

关键词：

D-galactose; thioglycoside; anchimeric assistance; C-6; substitution; cyanide;

D O I：

10.1016/S0008-6215(99)00048-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Nucleophilic displacement by the cyanide anion of the 6-O-triflyl group in phenyl 6-O-triflyl-2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-beta-D-galactopyranoside takes place via an intermediate 1,6-sulfonium salt resulting from the anchimeric assistance of the C-1 phenylthio group. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：201 / 205

页数：5

共 8 条

[1]

BORBAS A, 1994, ACH-MODELS CHEM, V131, P455

[2] NUCLEOPHILIC DISPLACEMENT REACTIONS IN CARBOHYDRATES .6. SOLVOLYSIS OF METHYL 2,3-DI-O-BENZYL-6-O-METHYLSULPHONYL-BETA-D-GALCTOPYRANOSIDE - PARTICIPATION BY A BENZYLOXY-GROUP [J].

BRIMACOM.JS ;

CHING, OA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (13) :1642-&

[3] ENANTIOSPECIFIC SYNTHESIS OF (+)-(6S,8R,E)-METHYL 2,3-DIDEHYDRONONACTATE [J].

DESCHENAUX, PF ;

JACOTGUILLARMOD, A .

HELVETICA CHIMICA ACTA, 1990, 73 (07) :1861-1864

[4]

LIPTAK A, 1983, ACTA CHIM HUNG, V113, P415

[5] NUCLEOPHILE INDUCED REARRANGEMENTS OF THIOGLYCOSIDES - FORMATION OF 6-THIO GLYCOSIDES AND 1,6-THIOANHYDROSUGARS [J].

LOWARY, TL ;

BUNDLE, DR .

TETRAHEDRON-ASYMMETRY, 1994, 5 (12) :2397-2404

[6] ETHYLATION OF THIOLAEVOGLUCOSAN TO A CRYSTALLINE SULFONIUM SALT AND REACTION OF THE LATTER WITH NUCLEOPHILES [J].

LUNDT, I ;

SKELBAEKPEDERSEN, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1981, 35 (09) :637-642

[7]

SHARMA M, 1987, CARBOHYD RES, V163, P41

[8] SULPHATES OF MONOSACCHARIDES AND DERIVATIVES .4. GALACTOSE 4-SULPHATE [J].

TURVEY, JR ;

WILLIAMS, TP .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (JUN) :2119-&

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