83 エナンチオ選択的アシル化による光学活性ミオ-イノシトール誘導体の調達とそれを利用するイノシトール三-および四リン酸の簡易合成(口頭発表の部)

概要

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Partial benzoylation of myo-inositol (4) with benzoyl chloride (3.5eg.) in pyridine at 90℃ afforded 1,3,4,5-tetrabenzoyl- (5) and 1,3,5-tribenzoyl-myo-inositol (6) as main products. Tetrabenzoate 5 was utilized for the synthesis of myo-inositol 1,4,5-tris(phosphate) (2) and myo-inositol 1,3,4,5-tetrakisphosphate (3) via silyl ethers 10 (Scheme 2). In the transformation, Grignard reagents were found to facilitate the removal of benzoyl groups in 10 without migration of silyl groups while conventional methods using alkoxide and ammonia gave a number of migration products. The reaction of symmetrical tribenzoate 6 with D- or L-tartaric acid derivative in the presence of methanesulfonyl chloride yielded monoacylation product D-7 or L-7 with high de (Table 1). Kinetic resolution of tetrabenzoate 5 using tartrate D-8 was also successfully accomplished (Scheme 1). Thus, straightforward protection of myo-inositol and efficient asymmetric preparation of optically active inositol derivatives have enabled the short-step and practical synthesis of 2 and 3.
天然有機化合物討論会の論文
1990-09-25