Synthesis of 7-Methyl-3-β-D-ribofuranosylwye, the Putative Structure for the Hypermodified Nucleoside Isolated from Archaebacterial Transfer Ribonucleic Acids

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The Vilsmeier-Haack reaction of 3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)wye (7c) followed successively by reduction with sodium borohydride and catalytic hydrogenolysis afforded the 7-methyl derivative 12c, which provided the title compound 12a on deprotection. Compound 12c was more effectively produced by direct hydrogenolysis of the 7-formyl derivative 8c, especially by use of Pearlman's catalyst. Similar treatment of 1-benzyl-7-formylwye (14) led to a better synthesis of 7-methylwye (1b), the fluorescent base isolated from Archabacterial transfer ribonucleic acids. Although hydrogenolysis of the 6-formyl compound 11 took place smoothly even over ordinary palladium on charcoal to afford 12c, this route had a bottleneck in the step of transformation of 8c into 11.Compound 12a proved to be highly sensitive to acidic hydrolysis at the glycosyl bond and the rate determined in 0.1N hydrochloric acid at 25℃was virtually the same as that of 3-β-D-ribofuranosylwye (7a).
公益社団法人日本薬学会の論文
1990-10-25