【药物名称】Forphenicinol, Forfenimex
化学结构式(Chemical Structure):
参考文献No.47245
标题:Pharmacological cpd. with immunopotentiating activity and production and uses thereof
作者:Aoyagi, T.; Ishizuka, M.; Matsumoto, I,. Morishima, H.; Takeuchi, T.; Umezawa, H.; Yamamoto, T. (Microbial Chemistry Research Foundation)
来源:US 4238507
合成路线图解说明:

The partial reduction of dimethyl hydroxyterephthalate (I) with NaBH4 in refluxing methanol gives methyl-3-hydroxy-4-(hydroxymethyl)benzoate (II), which by reaction with 2,2-dimethoxypropane (III) by means of p-toluenesulfonic acid in benzene is converted into the benzo-1,3-dioxane (IV). The reduction of (IV) with sodium dihydro-bis(2-methoxyethoxy)aluminate (V) affords the protected benzyl alcohol (VI), which is oxidized with CrO3 to the benzaldehyde (VII). The reaction of (VII) with NaCN and ammonia in methanol yields the aminonitrile (VIII), which is finally hydrolyzed with Ba(OH)2 and afterwards with H2SO4.

参考文献No.66389
标题:Forphenicinol
作者:Arrigoni-Martelli, E.; Casta馿r, J.; Serradell, M.N.; Blancafort, P.
来源:Drugs Fut 1983,8(7),587
合成路线图解说明:

The partial reduction of dimethyl hydroxyterephthalate (I) with NaBH4 in refluxing methanol gives methyl-3-hydroxy-4-(hydroxymethyl)benzoate (II), which by reaction with 2,2-dimethoxypropane (III) by means of p-toluenesulfonic acid in benzene is converted into the benzo-1,3-dioxane (IV). The reduction of (IV) with sodium dihydro-bis(2-methoxyethoxy)aluminate (V) affords the protected benzyl alcohol (VI), which is oxidized with CrO3 to the benzaldehyde (VII). The reaction of (VII) with NaCN and ammonia in methanol yields the aminonitrile (VIII), which is finally hydrolyzed with Ba(OH)2 and afterwards with H2SO4.

参考文献No.605730
标题:Synthesis of forphenicinol and forphenicine
作者:Morishima, H.; Yoshizawa, J.; Ushijima, R.; Takeuchi, T.; Umezawa, H.
来源:J Antibiot 1982,35(11),1500-06
合成路线图解说明:

The partial reduction of dimethyl hydroxyterephthalate (I) with NaBH4 in refluxing methanol gives methyl-3-hydroxy-4-(hydroxymethyl)benzoate (II), which by reaction with 2,2-dimethoxypropane (III) by means of p-toluenesulfonic acid in benzene is converted into the benzo-1,3-dioxane (IV). The reduction of (IV) with sodium dihydro-bis(2-methoxyethoxy)aluminate (V) affords the protected benzyl alcohol (VI), which is oxidized with CrO3 to the benzaldehyde (VII). The reaction of (VII) with NaCN and ammonia in methanol yields the aminonitrile (VIII), which is finally hydrolyzed with Ba(OH)2 and afterwards with H2SO4.

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