GENERAL-SYNTHESIS OF INOSITOLS BY HYDROLYSIS OF CONDURITOL EPOXIDES OBTAINED BIOCATALYTICALLY FROM HALOGENOBENZENES - (+)-D-CHIRO-INOSITOL, ALLO-INOSITOL, MUCO-INOSITOL AND NEO-INOSITOL

被引:55
作者
MANDEL, M [1 ]
HUDLICKY, T [1 ]
机构
[1] VIRGINIA POLYTECH INST & STATE UNIV,DEPT CHEM,BLACKSBURG,VA 24061
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 07期
关键词
D O I
10.1039/p19930000741
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four of the nine isomeric inositols have been prepared by hydrolytic opening of epoxides derived from 3-halogenocyclohexa-3,5-diene-1,2-diol by further oxidation with potassium permanganate or by reduction of chiro-3-inosose (2L-2,3,6/4,5-pentahydroxycyclohexanone).
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页码:741 / 743
页数:3
相关论文
共 47 条
[1]   CYCLITOLS .7. ANHYDROINOSITOLS AND THE EPOXIDE MIGRATION [J].
ANGYAL, SJ ;
GILHAM, PT .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3691-3699
[2]   CYCLITOLS .23. SUPPRESSION OF EPOXIDE MIGRATION . SYNTHESIS OF MUCOINOSITOL [J].
ANGYAL, SJ ;
BENDER, V ;
CURTIN, JH .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (08) :798-&
[3]   CONDURITOLS AND RELATED-COMPOUNDS [J].
BALCI, M ;
SUTBEYAZ, Y ;
SECEN, H .
TETRAHEDRON, 1990, 46 (11) :3715-3742
[4]  
BANWELL MG, 1992, J CHEM SOC P1, P1
[5]   INOSITOL PHOSPHATES AND CELL SIGNALING [J].
BERRIDGE, MJ ;
IRVINE, RF .
NATURE, 1989, 341 (6239) :197-205
[6]   RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES [J].
BILLINGTON, DC .
CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) :83-122
[7]   ENANTIOMERIC EXCESS AND ABSOLUTE-CONFIGURATION DETERMINATION OF CIS-DIHYDRODIOLS FROM BACTERIAL METABOLISM OF MONOCYCLIC ARENES [J].
BOYD, DR ;
DORRITY, MRJ ;
HAND, MV ;
MALONE, JF ;
SHARMA, ND ;
DALTON, H ;
GRAY, DJ ;
SHELDRAKE, GN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :666-667
[8]   A H-1-NMR METHOD FOR THE DETERMINATION OF ENANTIOMERIC EXCESS AND ABSOLUTE-CONFIGURATION OF CIS-DIHYDRODIOL METABOLITES OF POLYCYCLIC ARENES AND HETEROARENES [J].
BOYD, DR ;
SHARMA, ND ;
BOYLE, R ;
MCMORDIE, RAS ;
CHIMA, J ;
DALTON, H .
TETRAHEDRON LETTERS, 1992, 33 (09) :1241-1244
[9]   SYNTHESIS OF ARENE OXIDE AND TRANS-DIHYDRO DIOL METABOLITES OF ISOQUINOLINE [J].
BOYD, DR ;
DAVIES, RJH ;
HAMILTON, L ;
MCCULLOUGH, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :31-35
[10]  
BROWN SM, 1993, ARENECISDIOLS SYNTHE, V2, P113