The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphate

被引:11
|
作者
Desai, T [1 ]
Gigg, J [1 ]
Gigg, R [1 ]
MartinZamora, E [1 ]
机构
[1] NATL INST MED RES, DIV LIPID & GEN CHEM, LONDON NW7 1AA, ENGLAND
关键词
phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates; chiral myo-inositol derivatives; tin-mediated alkylations; allyl ethers; p-methoxybenzyl ethers; 1D-myo-inositol 1,3,4,5-tetrakisphosphate analogues;
D O I
10.1016/S0008-6215(96)00211-X
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
Details of the products obtained by the tin-mediated allylation and benzylation of 1,2-O-isopropylidene-myo-inositol, which were previously described in a preliminary communication, are provided here. Some of the products from these reactions, particularly 3,4,6-tri-O-allyl- and 3,5,6-tri-O-allyl-1,2-O-isopropylidene-myo-inositol, have been used to prepare intermediates for the synthesis of the title compounds. The syntheses of the following are described: 1L-2,4,5,6-tetra-O-benzyl-1-O-p-methoxybenzyl-myo-inositol (an intermediate for phosphatidylinositol 3-phosphate), 1L-2,4,5-tri-O-benzyl-myo-inositol 1,6-bis(dibenzyl phosphate) and IL-2,4,5-tri-O-benzyl-1,6-di-O-p-methoxybenzyl-myo-inositol (intermediates for phosphatidylinositol 3,4-bisphosphate), 1L-2,4-di-O-benzyl-myo-inositol 1,5,6-tris(dibenzyl phosphate) and(+/-)-2,4-di-O-benzyl-1,5,6-tri-O-p-methoxybenzyl-myo-inositol (intermediates for phosphatidylinositol 3,4,5-trisphosphate). Some of the intermediates used in the above preparations were also used for the synthesis of myo-inositol derivatives suitable for the preparation of analogues of 1D-myo-inositol 1,3,4,5-tetra-kisphosphate. Thus 1L-2,4-di-O-benzyl-5-O-p-methoxybenzyl-myo-inositol (for a 5-phosphorothioate analogue), crystalline 1L-2,5-di-O-beazyl-1-O-p-methoxybenzyl-myo-inositol 3,5,6-tris(dibenzyl phosphate), and crystalline 1D-2,6-di-O-benzyl-myo-inositol 1,4,5-tris(dibenzyl phosphate) (for a 3-phosphorothioate analogue) were prepared. The possibilities of using the latter compound in syntheses of tritium-labelled 1D-myo-inositol 1,4,5-trisphosphate and 1,3,4,5-tetrakisphosphate are discussed. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:97 / 133
页数:37
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