GLYCOSYLIMIDATES .51. SYNTHESIS OF BETA-O-GLYCOSIDES USING ENOL ETHER AND IMIDATE DERIVED LEAVING GROUPS - EMPHASIS ON THE USE OF NITRILES AS A SOLVENT

被引：91

作者：

VANKAR, YD ^{[1
]}

VANKAR, PS ^{[1
]}

BEHRENDT, M ^{[1
]}

SCHMIDT, RR ^{[1
]}

机构：

[1] UNIV CONSTANCE,FAK CHEM,W-7750 CONSTANCE,GERMANY

来源：

TETRAHEDRON | 1991年 / 47卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(01)96047-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new methods of beta-glycoside synthesis using donors 2 and 3 that contain leaving groups derived from enol ether and imidates have been developed. Effect of nitriles as a solvent in directing mainly beta-glycosidations has been compared with various methods reported in the literature. Effectiveness of leaving group at low temperatures and participation of nitriles in the formation of nitrilium-nitrile conjugate has been emphasized.

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页码：9985 / 9992

页数：8

相关论文

共 17 条

[1] DIRECT ELABORATION OF PENT-4-ENYL GLYCOSIDES INTO DISACCHARIDES [J].

FRASERREID, B ;

KONRADSSON, P ;

MOOTOO, DR ;

UDODONG, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :823-825

[2] A RAPID AND EFFICIENT SYNTHESIS OF 1,2-TRANS-BETA-LINKED GLYCOSIDES VIA BENZYL-PROTECTED OR BENZOYL-PROTECTED GLYCOPYRANOSYL PHOSPHATES [J].

HASHIMOTO, S ;

HONDA, T ;

IKEGAMI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :685-687

[3]

HASHIMOTO S, 1990, CHEM PHARM BULL, V38, P2323

[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] SULFENATE ESTERS AS GLYCOSYL ACCEPTORS - A NOVEL-APPROACH TO O-GLYCOSIDES FROM THIOGLYCOSIDES AND SULFENATE ESTERS [J].

ITO, Y ;

OGAWA, T .

TETRAHEDRON LETTERS, 1987, 28 (40) :4701-4704

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

KREUZER, M ;

THIEM, J .

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

[7]

MICHEL JA, 1983, THESIS U KONSTANZ

[8] STEREOSELECTIVE GLYCOSIDATIONS OF URONIC-ACIDS [J].

SCHMIDT, RR ;

RUCKER, E .

TETRAHEDRON LETTERS, 1980, 21 (15) :1421-1424

[9]

SCHMIDT RR, 1985, J CARBOHYD CHEM, V4, P141, DOI 10.1080/07328308508058829

[10]

SCHMIDT RR, 1990, SYNLETT, P694