A SIMPLE ROUTE FROM GLUCAL TO CERNY EPOXIDES

被引：18

作者：

LAUER, G ^{[1
]}

OBERDORFER, F ^{[1
]}

机构：

[1] DEUTSCH KREBSFORSCHUNGSZENTRUM,RADIOCHEM & RADIOPHARMAZEUT CHEM ABT,NEUENHEIMER FELD 280,W-6900 HEIDELBERG,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 02期

关键词：

D O I：

10.1002/anie.199302721

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Previously difficult to obtain, dianhydropyranoses 1 and 2 can now be synthesized from the pseudoglucal derivative 3 in one step with surprising ease and in good yields. The bridged glucoside 3 is prepared from glucal by an intramolecular ring-closure novel for this type of compound. R = H.(~)[GRAPHICS]

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页码：272 / 273

页数：2

相关论文

共 16 条

[1] ADDITION OF HALOGENOAZIDES TO GLYCALS [J].

BOVIN, NV ;

ZURABYAN, SE ;

KHORLIN, AY .

CARBOHYDRATE RESEARCH, 1981, 98 (01) :25-35

[2]

CERNY M, 1969, COLLECT CZECH CHEM C, V34, P849

[3]

CERNY M, 1969, COLLECT CZECH CHEM C, V34, P3377

[4]

CERNY M, 1977, ADV CARBOHYD CHEM BI, V34, P107

[5] SYNTHESES OF 3-DEOXY-3-SUBSTITUTED-D-GLUCOSE DERIVATIVES .1. IMPROVEMENTS IN PREPARATION OF AND NUCLEOPHILIC ADDITIONS TO 1,6-2,3-DIANHYDRO-4-O-BENZYL-BETA-D-ALLOPYRANOSE [J].

GRINDLEY, TB ;

REIMER, GJ ;

KRALOVEC, J ;

BROWN, RG ;

ANDERSON, M .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (05) :1065-1071

[6] OPTICALLY-ACTIVE KETONES CONTAINING A 6,8-DIOXABICYCLO[3.2.1]OCTANE SYSTEM .3. SYNTHESIS OF ISOMERIC ENONES OF 1,6-ANHYDRO-BETA-D-HEXOPYRANOSES [J].

KOLL, P ;

SCHULTEK, T ;

RENNECKE, RW .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (01) :337-344

[7]

MURRAY TP, 1974, CAN J CHEM, V49, P2132

[8] SYNTHESES WITH ANHYDRO SUGARS .15. SYNTHESES OF 1,6-ANHYDRO-2,3,4-TRIDEOXY-BETA-D-GLYCERO-HEXOPYRANOSE AND ITS UNSATURATED DERIVATIVES AS MODEL SUBSTANCES FOR STUDYING OPTICAL-ROTATION OF SUGARS [J].

PECKA, J ;

CERNY, M .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1973, 38 (01) :132-142

[9] HEXENOPYRANOSE DERIVATIVES OBTAINED BY ALLYLIC BROMINATION OF 6,8-DIOXABICYCLO[3.2.1]OCT-2-ENE AND 6,8-DIOXABICYCLO[3.2.1]OCT-3-ENE AND SUBSEQUENT BASIC SOLVOLYSIS OF PRODUCT [J].

RANGANAYAKULU, K ;

BROWN, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (26) :3941-3943

[10] BASE-CATALYZED ISOMERIZATION OF EPOXIDES TO BICYCLIC ALLYLIC ALCOHOLS, POTENTIAL INTERMEDIATES FOR TOTAL SYNTHESIS OF DL-ALDOHEXOSES [J].

RANGANAYAKULU, K ;

SINGH, UP ;

MURRAY, TP ;

BROWN, RK .

CANADIAN JOURNAL OF CHEMISTRY, 1974, 52 (06) :988-992