Studies towards the synthesis of the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid: Improved synthesis of the base β-hydroxywybutine

Article abstract of DOI:10.1248/cpb.46.1220

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(Phc), has been achieved by the Wittig reaction between 1-benzyl-7-formylwye (1) and the phosphorane derived from (R)-2[(methoxycarbonyl)amino]-3- (triphenylphosphonio)propanoate (10), followed by methylation, OsO₄ oxidation, and cyclocondensation with COCI₂ 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 NaBH₄ reduction and catalytic hydrogenolysis. The samples of [R-(R*,S*)]- and [S-(R*,R*)]-4 were thus shown to be optically pure.

Full text of DOI:10.1248/cpb.46.1220

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