REACTION OF SULFUR YLIDES WITH REDUCING CARBOHYDRATES - APPLICATION TO SYNTHESIS OF HYDROXYMETHYL-C-GLYCOSIDES

被引：25

作者：

FRECHOU, C

DHEILLY, L

BEAUPERE, D

UZAN, R

DEMAILLY, G

机构：

[1] Laboratoire de Chimie Organique, Groupe de Valorisation des Glucides, Faculté des Sciences, 80039 Amiens

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 35期

关键词：

HYDROXYMETHYL C-GLYCOSIDES; TRIMETHYLSULFOXONIUM YLIDE; TRIMETHYLSULFONIUM YLIDE; EPOXY ALCOHOL;

D O I：

10.1016/S0040-4039(00)61191-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of reducing carbohydrates with unstabilized sulfur ylides affords epoxy alcohols. When the reaction is not accompanied by elimination of a leaving group at C-3, spontaneous cyclisation occurs, and hydroxymethyl C-glycosyl compounds are obtained.

引用

收藏

页码：5067 / 5070

页数：4

相关论文

共 22 条

[1] THE WITTIG-HORNER REACTION ON 2,3,4,6-TETRA-O-BENZYL-D-MANNOPYRANOSE AND 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE [J].

ALLEVI, P ;

CIUFFREDA, P ;

COLOMBO, D ;

MONTI, D ;

SPERANZA, G ;

MANITTO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07) :1281-1283

[2] DEOXY-NITROSUGARS .6. STEREOELECTRONIC CONTROL IN THE REDUCTIVE DENITRATION OF TERTIARY NITRO ETHERS - A SYNTHESIS OF C-GLYCOSIDES [J].

BAUMBERGER, F ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1983, 66 (07) :2210-2222

[3] VINYLATION ELECTROPHILIC CYCLIZATION OF ALDOPENTOSES - EASY AND STEREOSELECTIVE ACCESS TO C-GLYCOPYRANOSIDES OF RARE SUGARS [J].

BOSCHETTI, A ;

NICOTRA, F ;

PANZA, L ;

RUSSO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4181-4185

[4]

BRAVO P, 1968, J CHEM SOC CHEM COMM, P1311

[5] STEREOCONTROLLED ROUTES TO FUNCTIONALIZED C-GLYCOPYRANOSIDES [J].

DAWE, RD ;

FRASERREID, B .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :522-528

[6] A NEW ROUTE TO C-GLYCOSYL COMPOUNDS - WITTIG-TYPE REACTION PROMOTED BY ZINC [J].

DHEILLY, L ;

FRECHOU, C ;

BEAUPERE, D ;

UZAN, R ;

DEMAILLY, G .

CARBOHYDRATE RESEARCH, 1992, 224 :301-306

[7] STEREOSELECTIVE ROUTES TO SOME UNSATURATED ALPHA-C-GLYCOPYRANOSIDES AND BETA-C-GLYCOPYRANOSIDES [J].

FRASERREID, B ;

DAWE, RD ;

TULSHIAN, DB .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (13) :1746-1749

[8] 25 YEARS OF DIMETHYLSULFOXONIUM METHYLIDE (COREYS REAGENT) [J].

GOLOLOBOV, YG ;

NESMEYANOV, AN ;

LYSENKO, VP ;

BOLDESKUL, IE .

TETRAHEDRON, 1987, 43 (12) :2609-2651

[9] PYRAZOMYCIN B - ISOLATION AND CHARACTERIZATION OF AN ALPHA-C-NUCLEOSIDE ANTIBIOTIC RELATED TO PYRAZOMYCIN [J].

GUTOWSKI, GE ;

CHANEY, MO ;

JONES, ND ;

HAMILL, RL ;

DAVIS, FA ;

MILLER, RD .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1973, 51 (02) :312-317

[10] PREPARATIVE AND EXPLORATORY CARBOHYDRATE CHEMISTRY - FACILE ACCESS TO ETHYL 2-C-BETA-D-RIBOFURANOSYLACETATES [J].

HANESSIAN, S ;

OGAWA, T ;

GUINDON, Y .

CARBOHYDRATE RESEARCH, 1974, 38 (01) :C12-C14