Misoprostol, SC-29333, Misopess, Cytotec
米索前列醇Chemical Name: (?-15-Deoxy-16(RS)-hydroxy-16-methyl-PGE1 methyl ester; (11alpha,13E)-(?-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oic acid methyl ester; (?-(1R,2R,2R)-7-[3-Hydroxy-2-[(4RS)-4-hydroxy-4-methyl-1(E)-octenyl]-5-oxocyclopentyl]heptanoic acid methyl ester
CAS No. 59122-46-2
项目整合开发状态: Launched-1985
项目研究机构: Pfizer (Originator), Xanodyne (Licensee), Cytokine PharmaSciences (Formulation)
合成路线:The sililation of 4-methyl-1-octin-4-ol (I) with trimethylsilyl chloride by means of triethylamine in DMF gives the corresponding silyloxy derivative (II),which is treated with diisobutyl aluminum hydride and I2 in toluene - THF yielding 4-methyl-(RS)-4-trimethylsilyloxy-trans-1-octene-1-yl iodide (III).The condensation of (III) with the complex of copper 1-pentynilyde and HMPT (IV) by means of butyllithium in hexane affords the complex salt (V),which,without isolation,is allowed to react with methyl 7-[3-[(RS)-tetrahydropyranyl-2-oxy]-5-oxo-1-cyclopentenyl]-heptanoate (VI) in ethyl ether to give methyl 7-[3-(tetrahydropyranyl-2-oxy)-2-(4-methyl-4-trimethylsilyloxy-trans-1-octene-1-yl)-5-oxo-cyclopentyl]heptanoate (VII).Finally,this compound is hydrolyzed with a mixture acetic acid - water - THF at room temperature.
📌 参考资料/链接：
参考文献标题:SC-29333
文献作者:Castar,J.; Hillier,K.
参考来源:Drugs Fut 1977,2(12),817
📄 详细内容
合成路线:The sililation of 4-methyl-1-octin-4-ol (I) with trimethylsilyl chloride by means of triethylamine in DMF gives the corresponding silyloxy derivative (II),which is treated with diisobutyl aluminum hydride and I2 in toluene - THF yielding 4-methyl-(RS)-4-trimethylsilyloxy-trans-1-octene-1-yl iodide (III).The condensation of (III) with the complex of copper 1-pentynilyde and HMPT (IV) by means of butyllithium in hexane affords the complex salt (V),which,without isolation,is allowed to react with methyl 7-[3-[(RS)-tetrahydropyranyl-2-oxy]-5-oxo-1-cyclopentenyl]-heptanoate (VI) in ethyl ether to give methyl 7-[3-(tetrahydropyranyl-2-oxy)-2-(4-methyl-4-trimethylsilyloxy-trans-1-octene-1-yl)-5-oxo-cyclopentyl]heptanoate (VII).Finally,this compound is hydrolyzed with a mixture acetic acid - water - THF at room temperature.
参考文献标题:16-Oxygenated prostanoic acid derivatives
文献作者:Pappo,R.; Collins,P.W.
参考来源:BE 0827127; DE 2513212; FR 2274289; GB 1492426; JP 50135059; US 3965143
合成路线:The sililation of 4-methyl-1-octin-4-ol (I) with trimethylsilyl chloride by means of triethylamine in DMF gives the corresponding silyloxy derivative (II),which is treated with diisobutyl aluminum hydride and I2 in toluene - THF yielding 4-methyl-(RS)-4-trimethylsilyloxy-trans-1-octene-1-yl iodide (III).The condensation of (III) with the complex of copper 1-pentynilyde and HMPT (IV) by means of butyllithium in hexane affords the complex salt (V),which,without isolation,is allowed to react with methyl 7-[3-[(RS)-tetrahydropyranyl-2-oxy]-5-oxo-1-cyclopentenyl]-heptanoate (VI) in ethyl ether to give methyl 7-[3-(tetrahydropyranyl-2-oxy)-2-(4-methyl-4-trimethylsilyloxy-trans-1-octene-1-yl)-5-oxo-cyclopentyl]heptanoate (VII).Finally,this compound is hydrolyzed with a mixture acetic acid - water - THF at room temperature.
参考文献标题:Influence of the position of the side-chain hydroxy group on the biological properties of prostaglandins
文献作者:Collins,P.W.; et al.
参考来源:Tetrahedron Lett 1975,484217-20
产品链接: CAS No. 59122-46-2››