beta-selective C-glycosidations: Lewis-acid mediated reactions of carbohydrates with silyl ketene acetals

被引：43

作者：

Minehan, TG ^{[1
]}

Kishi, Y ^{[1
]}

机构：

[1] HARVARD UNIV,DEPT CHEM & CHEM BIOL,CAMBRIDGE,MA 02138

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 39期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01602-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several examples of beta-selective C-glycosidation reactions, involving TMSOTf-promoted addition of sterically hindered silyl ketene acetals to glucosyl and galactosyl acetates, are presented. (C) 1997 Elsevier Science Ltd.

引用

页码：6815 / 6818

页数：4

共 11 条

[1] CHEMISTRY OF ORGANO-SILICON COMPOUNDS .194. HIGHLY STEREOSELECTIVE C-ALLYLATION OF GLYCOPYRANOSIDES WITH ALLYLSILANES CATALYZED BY SILYL TRIFLATE OR IODOSILANE [J].

HOSOMI, A ;

SAKATA, Y ;

SAKURAI, H .

TETRAHEDRON LETTERS, 1984, 25 (22) :2383-2386

[2] A MILD METHOD FOR THE SYNTHESIS OF ANOMERICALLY ALLYLATED C-GLYCOPYRANOSIDES AND C-GLYCOFURANOSIDES [J].

KOZIKOWSKI, AP ;

SORGI, KL .

TETRAHEDRON LETTERS, 1982, 23 (22) :2281-2284

[3]

Levy D.E., 1995, CHEM C GLYCOSIDES

[4] HIGHLY STEREOSELECTIVE APPROACHES TO ALPHA-C-GLYCOPYRANOSIDE AND BETA-C-GLYCOPYRANOSIDE [J].

LEWIS, MD ;

CHA, JK ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4976-4978

[5] NUCLEOPHILIC ADDITIONS TO THIONOLACTONES - NEW SYNTHETIC TECHNOLOGY FOR THE CONSTRUCTION OF MEDIUM-RING AND LARGE-RING ETHERS [J].

NICOLAOU, KC ;

MCGARRY, DG ;

SOMERS, PK ;

VEALE, CA ;

FURST, GT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2504-2506

[6]

POSTEMA MHD, 1995, C GLCYOSIDE SYNTHESI

[7] Synthesis of beta-C-glycosides of N-acetylglucosamine via Keck allylation directed by neighboring phthalimide groups [J].

Roe, BA ;

Boojamra, CG ;

Griggs, JL ;

Bertozzi, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6442-6445

[8] GLYCOSYLIMIDATES .5. C-GLYCOSIDES FROM O-GLYCOSYL TRICHLOROACETIMIDATES [J].

SCHMIDT, RR ;

HOFFMANN, M .

TETRAHEDRON LETTERS, 1982, 23 (04) :409-412

[9] HIGHLY SELECTIVE FORMATION OF A BETA-C-GLUCOSIDIC BOND IN THE REACTIONS OF ARSCL-GLUCAL ADDUCTS WITH SILICON-CONTAINING NUCLEOPHILES [J].

SMOLIAKOVA, IP ;

CAPLE, R ;

GREGORY, D ;

SMIT, WA ;

SHASHKOV, AS ;

CHIZHOV, OS .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1221-1227

[10] C-GLYCOSIDATION OF PYRIDYL THIOGLYCOSIDES [J].

STEWART, AO ;

WILLIAMS, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4289-4296

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