Forphenicinol, Forfenimex
福芬诺尔 福酚美克 Chemical Name: L-2-(3-Hydroxy-4-hydroxymethylphenyl)glycine; (-)-(R)-alpha-Amino-3-hydroxy-4-(hydroxymethyl)benzeneacetic acid
CAS No. 71522-58-2, 72973-11-6 ((+)-enantiomer)
项目整合开发状态: Phase III
项目研究机构: Banyu (Originator), Nippon Kayaku (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Pharmacological cpd.with immunopotentiating activity and production and uses thereof
文献作者:Aoyagi,T.; Ishizuka,M.; Matsumoto,I,.Morishima,H.; Takeuchi,T.; Umezawa,H.; Yamamoto,T.(Microbial Chemistry Research Foundation)
参考来源:US 4238507
📄 详细内容
合成路线: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.
参考文献标题:Forphenicinol
文献作者:Arrigoni-Martelli,E.; Castar,J.; Serradell,M.N.; Blancafort,P.
参考来源:Drugs Fut 1983,8(7),587
合成路线: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.
参考文献标题:Synthesis of forphenicinol and forphenicine
文献作者:Morishima,H.; Yoshizawa,J.; Ushijima,R.; Takeuchi,T.; Umezawa,H.
参考来源:J Antibiot 1982,35(11),1500-06
产品链接: CAS No. 71522-58-2›› 产品链接: CAS No.72973-11-6››