Studies towards the Synthesis of the Hypermodified Nucleoside of Rat Liver Phenylalanine Transfer Ribonucleic Acid : Improved Synthesis of the Base β-Hydroxywybutine

概要

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An improved synthesis of the key intermediates (3 and 8) for the synthesis of β-hydroxywybutines [[R-(R^*, S^*)]- and [S-(R^*, R^*)]-4], the most probable structures for the minor base from rat liver tRNA^<Phe>, has been achieved by the Witting reaction between 1-benzyl-7-formylwye (1) and the phosphorane derived from (R)-2-[(methoxycarbonyl)amino]-3-(triphenylphosphonio)propanoate (10), followed by methylation, OsO_4 oxidation, and cyclocondensation with COCl_2 in the presence of pyridine. The racemic forms of β-hydroxywybutines [(R^*, S^*)- and (R^*, R^*)-4], which were required for the determination of the optical purity of [R-(R^*, S^*)]- and [S-(R^*, R^*)]-4 by means of chiral HPLC, were conveniently prepared through pyrolysis of the cyclic carbonate 3 followed by NaBH_4 reduction and catalytic hydrogenolysis. The samples of [R-(R^*, S^*)]- and [S-(R^*, R^*)]-4 were thus shown to be optically pure.
公益社団法人日本薬学会の論文
1998-08-15