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
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.
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收藏
页码:197 / 209
页数:13
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