THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY .29. THE PREPARATION OF INTERMEDIATES FOR THE SYNTHESIS OF 1D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND 2,4,5-TRISPHOSPHATE, 1,4-BISPHOSPHATE 5-PHOSPHOROTHIOATE, AND 4,5-BISPHOSPHATE 1-PHOSPHOROTHIOATE FROM 1D-3,6-DI-O-BENZYL-1,2-O-ISOPROPYLIDENE-MYO-INOSITOL

被引：20

作者：

DESAI, T ^{[1
]}

GIGG, J ^{[1
]}

GIGG, R ^{[1
]}

MARTINZAMORA, E ^{[1
]}

机构：

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

来源：

CARBOHYDRATE RESEARCH | 1994年 / 262卷 / 01期

关键词：

MYOINOSITOL PHOSPHATES; MYOINOSITOL PHOSPHOROTHIOATES; CHIRAL MYOINOSITOL DERIVATIVES; ALLYL ETHERS; CROTYL ETHERS;

D O I：

10.1016/0008-6215(94)84005-9

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：

The preparation of 1D-1,6-di-O-benzyl-2,5-di-O-p-methoxybenzyl-myo-inositol is described. This compound and 1D-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol were converted into 1D-1,3,6-tri-O-benzyl-myo-inositol which was phosphorylated to give an intermediate for the synthesis of 1D-myo-inositol 2,4,5-trisphosphate. 1D-3,6-Di-O-benzyl 1,2-O-isopropylidene-myo-inositol was converted into 1D-2,3,6-tri-O-benzyl-myo-inositol (an intermediate for the synthesis of 1D-myo-inositol 1,4,5-trisphosphate) and 1D-2,3,6-tri-O-benzyl-1-O-p-methoxybenzyl-myo-inositol (an intermediate for the synthesis of the 1-phosphorothioate analogue of 1D-myo-inositol 1,4,5-trisphosphate). 1D-3,6-Di-O-benzyl-1,2-O-isopropylidene-myo-inositol was also converted into 1D-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl[and -5-O(cis-prop-1-enyl)]-myo-inositol both of which are intermediates for the synthesis of the 5-phosphorothioate analogue of 1D-myo-inositol 1,4,5-trisphosphate. The synthesis of 1D-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) 5-(dibenzyl phosphorothioate) from 1D-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) is described.

引用

页码：59 / 77

页数：19

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