ORGANOALUMINUM INDUCED RING-OPENING OF EPOXYPYRANOSIDES .4. SYNTHESIS AND STRUCTURE OF GAMMA-HYDROXY-ISOLEUCINE STEREOISOMERS AND THEIR CORRESPONDING LACTONES

被引：19

作者：

INGHARDT, T ^{[1
]}

FREJD, T ^{[1
]}

SVENSSON, G ^{[1
]}

机构：

[1] LUND INST TECHNOL,CTR CHEM,POB 124,S-22100 LUND,SWEDEN

来源：

TETRAHEDRON | 1991年 / 47卷 / 32期

关键词：

TRIMETHYLALUMINUM; OPENING OF EPOXIDE AND PYRANOSIDE RINGS; 2,3-ANHYDRO-BETA-L-RIBOPYRANOSIDE; GAMMA-HYDROXY-ISOLEUCINE; X-RAY DATA;

D O I：

10.1016/S0040-4020(01)86574-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two gamma- hydroxy-isoleucine stereoisomers 8 (2R, 3R, 4R), and 14 (2S, 3R, 4R) as well as their corresponding gamma- lactones 9 and 15 were synthesized using a tandem, Me3Al induced opening of the epoxide and pyranoside rings of benzyl 2,3-anhydro-4-O-(tert-butyldimethylsilyl)-beta-L-ribopyranoside (1). The structure of the lactone hydrochloride 9 was confirmed by an X-ray crystal structure determination.

引用

页码：6469 / 6482

页数：14

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