RARE-EARTH PERCHLORATE CATALYZED GLYCOSIDATION OF GLYCOSYL FLUORIDES WITH TRIMETHYLSILYL ETHERS

被引：33

作者：

KIM, WS ^{[1
]}

HOSONO, S ^{[1
]}

SASAI, H ^{[1
]}

SHIBASAKI, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 25期

关键词：

D O I：

10.1016/0040-4039(95)00760-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A glycosidation of glycosyl fluorides with trimethylsilyl ethers has been found to be promoted more effectively by catalytic La(ClO4)(3) than by stoichiometric amounts of rare earth salts. A mechanism for the present glycosidation is proposed.

引用

页码：4443 / 4446

页数：4

共 21 条

[1]

BERNARDO PD, 1991, INORG CHIM ACTA, V207, P85

[2] FT-IR AND FLUOROMETRIC INVESTIGATION OF RARE-EARTH AND METAL-ION SOLVATION .10. INNER-SPHERE INTERACTION BETWEEN PERCHLORATE AND LANTHANIDE IONS IN ANHYDROUS ACETONITRILE [J].

BUNZLI, JCG ;

KASPAREK, V .

INORGANICA CHIMICA ACTA, 1991, 182 (01) :101-107

[3]

BUNZLI JCG, 1982, INORG CHEM, V21, P1471

[4] GLYCOSYLATION USING GLUCOPYRANOSYL FLUORIDES AND SILICON-BASED CATALYSTS - SOLVENT DEPENDENCY OF THE STEREOSELECTION [J].

HASHIMOTO, S ;

HAYASHI, M ;

NOYORI, R .

TETRAHEDRON LETTERS, 1984, 25 (13) :1379-1382

[5] SIMPLE SYNTHESIS OF GLYCOSYL FLUORIDES [J].

HAYASHI, M ;

HASHIMOTO, S ;

NOYORI, R .

CHEMISTRY LETTERS, 1984, (10) :1747-1750

[6] A NEW GLYCOSYLATION PROCEDURE UTILIZING RARE-EARTH SALTS AND GLYCOSYL FLUORIDES, WITH OR WITHOUT THE REQUIREMENT OF LEWIS-ACIDS [J].

HOSONO, S ;

KIM, WS ;

SASAI, H ;

SHIBASAKI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :4-5

[7] GALLIUM REAGENTS IN ORGANIC-SYNTHESIS - DIMETHYLGALLIUM CHLORIDE AND TRIFLATE AS ACTIVATORS IN GLYCOSIDATION USING GLYCOPYRANOSYL FLUORIDES [J].

KOBAYASHI, S ;

KOIDE, K ;

OHNO, M .

TETRAHEDRON LETTERS, 1990, 31 (17) :2435-2438

[8]

KONIGS W, 1901, BER, V34, P957

[9] IODONIUM ION GENERATED INSITU FROM N-IODOSUCCINIMIDE AND TRIFLUOROMETHANESULFONIC ACID PROMOTES DIRECT LINKAGE OF DISARMED PENT-4-ENYL GLYCOSIDES [J].

KONRADSSON, P ;

MOOTOO, DR ;

MCDEVITT, RE ;

FRASEREID, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (03) :270-272

[10] THE COMPOSITION OF OLIGOSACCHARIDES WITH GLYCOSYLFLUORIDES DURING LEWIS ACID CATALYSIS [J].

KREUZER, M ;

THIEM, J .

CARBOHYDRATE RESEARCH, 1986, 149 (02) :347-361

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