THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .23. THE ALLYLATION OF DIBUTYLSTANNYLENE DERIVATIVES OF MYOINOSITOL

被引：15

作者：

DESAI, T ^{[1
]}

GIGG, J ^{[1
]}

GIGG, R ^{[1
]}

PAYNE, S ^{[1
]}

PENADES, S ^{[1
]}

ROGERS, HJ ^{[1
]}

机构：

[1] NATL INST MED RES,LIPID & GEN CHEM LAB,MILL HILL,LONDON NW7 1AA,ENGLAND

来源：

CARBOHYDRATE RESEARCH | 1991年 / 216卷

关键词：

D O I：

10.1016/0008-6215(92)84162-L

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reaction of myo-inositol or a mixture of racemic 1,4-, 1,6-, and 4,5-di-O-allyl-myo-inositol in acetonitrile with dibutyltin oxide and allyl bromide in the presence of tetrabutylammonium bromide gave, as the major products, a readily separable mixture of 1,3,4,6- and 1,3,4,5-tetra-O-allyl-myo-inositol together with small proportions of penta-O-allyl-myo-inositols and 1,3,5-tri-O-allyl-myo-inositol (from myo-inositol). Parallel results were obtained when crotyl bromide was used. When 3 equiv. of dibutyltin oxide were used with myo-inositol or 1 equiv. with the mixture of di-O-allyl derivatives, 1,3,4-tri-O-allyl-myo-inositol was the major product. When 2 equiv. of dibutyltin oxide were used, myo-inositol gave a complex mixture of mono-, di-, and tri-O-allyl derivatives which was fractionated after conversion into the O-isopropylidene derivatives. Racemic 1,3,4,5-tetra-O-allyl-myo-inositol was resolved via the (-)-omega-camphanates.

引用

页码：197 / 209

页数：13

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