SEQUENTIAL DIASTEREOSELECTIVE FREE-RADICAL REACTIONS - SYNTHESIS OF AN ADVANCED OLIVOMYCIN-A C-D-DISACCHARIDE

被引：28

作者：

CRICH, D

HERMANN, F

机构：

[1] Department of Chemistry (M/C 111), University of Illinois at Chicago, 801 W. Taylor, Rm 4500, Chicago

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(00)79162-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of an advanced olivomycin A C-D disaccharide is described in which the anomeric configuration of both 2-deoxy-beta-glycosidic linkages is determined by a sequential diastereoselective radical reaction at the end of the synthesis.

引用

页码：3385 / 3388

页数：4

共 58 条

[1] SYNTHESIS AND STRUCTURAL-ANALYSIS USING 2-D NMR OF SIALYL LEWIS-X (SLE(X)) AND LEWIS-X (LE(X)) OLIGOSACCHARIDES - LIGANDS RELATED TO E-SELECTIN [ELAM-1] BINDING [J].

BALL, GE ;

ONEILL, RA ;

SCHULTZ, JE ;

LOWE, JB ;

WESTON, BW ;

NAGY, JO ;

BROWN, EG ;

HOBBS, CJ ;

BEDNARSKI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5449-5451

[2]

Barton D. H. R., 1990, ALDRICHIM ACTA, V23, P3

[3] NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941

[4] THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].

BARTON, DHR ;

CRICH, D ;

MOTHERWELL, WB .

TETRAHEDRON, 1985, 41 (19) :3901-3924

[5] AGLYCON-DISACCHARIDE COUPLING IN MITHRAMYCIN ANALOG SYNTHESIS [J].

BINKLEY, RW .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (04) :507-511

[6] INVERSION OF CONFIGURATION IN 2,6-DIDEOXY SUGARS - TRIFLATE DISPLACEMENT BY BENZOATE AND NITRITE ANIONS [J].

BINKLEY, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3892-3896

[7] STUDIES ON UNSATURATED SUGARS WITH PARTICULAR REFERENCE TO SYNTHESIS OF 6-DEOXY-6-FLUORO DERIVATIVES [J].

BLACKBURNE, ID ;

FREDERICKS, PM ;

GUTHRIE, RD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (02) :381-391

[8] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].

BOLITT, V ;

MIOSKOWSKI, C ;

LEE, SG ;

FALCK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813

[9] SYNTHESIS OF LD-HEPP AND KDO CONTAINING DISACCHARIDE AND TETRASACCHARIDE DERIVATIVES OF NEISSERIA-MENINGITIDIS INNER-CORE REGION VIA IODONIUM ION PROMOTED GLYCOSIDATIONS [J].

BOONS, GJPH ;

VANDELFT, FL ;

VANDERKLEIN, PAM ;

VANDERMAREL, GA ;

VANBOOM, JH .

TETRAHEDRON, 1992, 48 (05) :885-904

[10] 1,2-STEREOINDUCTION IN RADICAL REACTIONS - STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXYBUTANOATES [J].

BULLIARD, M ;

ZEHNDER, M ;

GIESE, B .

HELVETICA CHIMICA ACTA, 1991, 74 (07) :1600-1607

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