Studies on the synthesis of the hypermodified base isolated from rat liver phenylalanine transfer ribonucleic acid
Itaya, T.; Watanabe, N.; Mizutani, A.
Nucleic Acids Symposium Series 17: 49-51
1986
ISSN/ISBN: 0261-3166 PMID: 3645548 Document Number: 280008
Oxidation of methyl (S,E)-4-[4,9-dihydro-4,6-dimethyl-9-oxo-1- (phenylmethyl)-1H-imidazo[1,2-alpha]purine-7-yl]-2-[(methoxycarbonyl) amino]-3-butenoate (3) with osmium tetroxide/N-methylmorpholine N-oxide provided a mixture of diastereomers 4 and 7. Hydrogenolysis of the major dihydroxy compound 4 over Pd-C gave beta-hydroxywybutine [[R-(R*,S*)]-1]. The minor isomer 7 was transformed into [S-(R*,R*)]-1 through the cyclic carbonate 8.