Synthesis of 2-Methoxyinosine and Its 5'-Phosphate

抄録

2, 6-Dichloro-9-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl) purine (I), when treated with 0.5 N barium hydroxide, afforded 2-chloroinosine (II), which was also obtained by reaction of I with 2 moles of methanolic sodium hydroxide followed by alkaline hydrolysis via 6-methoxy derivative (IV). Compound II was converted with sodium methoxide to 2-methoxyinosine (V). Alternatively, V was prepared by treating of I with the excess of methanolic sodium hydroxide. Compound V was allowed to react with acetone in the presence of 2, 2-dimethoxypropane and then phosphorylated with phosphoryl chloride to give, after deacetonation, 2-methoxyinosine 5'-phosphate (VIII). The synergistic flavoring strength of VIII with monosodium L-glutamate (MSG) was evaluated as an analog of 2-methylthioinosine 5'-phosphate or xanthosine 5'-phosphate. Similarly, 2-chloroinosine 5'-phosphate (IX) was synthesized from II and its flavoring strength was evaluated.