REACTIONS OF 2,3-O-ISOPROPYLIDENE DERIVATIVES OF FURANOSE SUGARS WITH ORGANOMAGNESIUM AND ORGANOLITHIUM NUCLEOPHILES

被引：51

作者：

MEKKI, B

SINGH, G

WIGHTMAN, RH

机构：

[1] TEESSIDE POLYTECH,SCH SCI & TECHNOL,MIDDLESBROUGH TS1 3BA,CLEVELAND,ENGLAND

[2] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)93450-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of 2,3-OMICRON-isopropylidene derivatives of furanose sugars with Grignard reagents afford stereoselectively products with an anti-(erythro-) relationship between the new chiral centre and that at C-2; the corresponding reactions with organolithium reagents are more variable stereochemically, but some predictive guidelines can be established.

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页码：5143 / 5146

页数：4

相关论文

共 20 条

[1]

BALLARD J M, 1970, Carbohydrate Research, V12, P37, DOI 10.1016/S0008-6215(00)80223-2

[2]

BOKOWNIK RR, 1988, J ORG CHEM, V58, P463

[3] C-NUCLEOSIDE STUDIES .2. PENTOFURANOSYLETHYNES FROM 2,3-O-ISOPROPYLIDENE-D-RIBOSE [J].

BUCHANAN, JG ;

DUNN, AD ;

EDGAR, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1191-1200

[4] ENATIOSPECIFIC SYNTHESIS OF (+)-RETRONECINE, (+)-CROTONECINE, AND RELATED ALKALOIDS [J].

BUCHANAN, JG ;

JIGAJINNI, VB ;

SINGH, G ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2377-2384

[5] C-NUCLEOSIDE STUDIES .3. GLYCOFURANOSYLETHYNES FROM 2,3-5,6-DI-O-ISOPROPYLIDENE-D-MANNOSE [J].

BUCHANAN, JG ;

DUNN, AD ;

EDGAR, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (01) :68-75

[6] TOTAL SYNTHESIS OF APLASMOMYCIN - STEREOCONTROLLED CONSTRUCTION OF THE C(3)-C(17) FRAGMENT [J].

COREY, EJ ;

PAN, BC ;

HUA, DH ;

DEARDORFF, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6816-6818

[7]

Hanessian S., 1983, TOTAL SYNTHESIS NATU

[8]

Hughes N.A., 1965, CARBOHYD RES, V1, P171

[9] THE PREPARATION AND UTILITY OF ETHYL 2-(5'-O-TERT-BUTYLDIMETHYLSILYL-2',3'-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)PROPENOATE AS A KEY INTERMEDIATE FOR C-NUCLEOSIDE SYNTHESIS [J].

KANE, PD ;

MANN, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04) :657-660

[10] BEHAVIOR OF SOME ALDOSES WITH 2,2-DIALKOXYPROPANE-N,N-DIMETHYLFORMAMIDE-PARA-TOLUENE-SULFONIC ACID .5. ACETONATION OF SOME PENTOSES WITH 2,2-DIMETHOXYPROPANE-N,N-DIMETHYLFORMAMIDE-PARA-TOLUENESULFONIC ACID [J].

KISO, M ;

HASEGAWA, A .

CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :95-101