66(P1-14) ミオ-イノシトールの直接的かつ効率的保護化とイノシトールリン酸類の合成(ポスター発表の部)

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Chemical synthesis of myo-inositol phosphates which are involved as metabolites in the intracellular signal transduction system have been accomplished during last three years by several groups. We have continuously made efforts to explore practical syntheses of them. The direct reaction of myo-inositol itself with an adequate electrophile may be a powerful tool for this purpose. Among electrophiles employed here, 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane(TIPSCl) was found to be especially pomising. Thus, the reaction of myo-inositol with 2.5 molar equivalent of TIPSCl in pyridine gave almost exclusively 1,6:3,4-di-TIPS derivative 20 in 66% yield. This product 20 was effectively utilized for the synthesis of myo-inositol 1,3,4,6-tetrakisphosphate 24, which was discovered recently. The reaction with benzoyl chloride was also useful. When the reaction was conducted at 90℃, 1,3,4,5-tetra-O-benzoyl-myo-inositol 25 was isolated as a main product by flashchromatography. 25 was quite easily converted to myo-inositol 1,3,4,5-tetrakisphosphate 31.
天然有機化合物討論会の論文
1989-09-17