79 ミオ-イノシトールリン酸類の合成

概要

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It has been found that D-myo-inositol 1,4,5-trisphosphate 1 acts as a cellular second messenger. Recent investigation has suggested that 2,4,5-trisphosphate 2 and 1,3,4,5-tetrakisphosphate 3 have a similar biological activity. Establishment of the metabolic pathway which involves these metabolites is required at the present time. For this purpose, we have tried to synthesize them. This time, first chemical syntheses of trisphosphates 1 and 2 are described. Starting from myo-inositol which is readily available, 1,2-diol 10a,b and 10'a,b were prepared. These racemates were optically resolved with ease by derivatization of them to 1-menthoxyacetic esters 14 and 15. Optically pure diol 10a obtained by hydrolysis of 14a was then transformed to a key intermediate, triol 20 by selective allylation, benzylation and deallylation. Phosphorylation of 20 was achieved by the use of dianilidophosphoric chloride 23. Deprotection of 24 gave 1. Menthoxyacetic esters(1:1 mixture of 14b and 15b) were phosphorylated by successive treatment with PCl_33, PhCH_2OH and t-BuO_2H to give dibenzyl phosphate 25. Selective removal of the methoxybenzyl group in 25 and stepwise phosphorylation (Scheme 7) gave the fully protected trisphosphate 28. Deprotection is now under way.
天然有機化合物討論会の論文
1986-09-09