【药物名称】TMA-230
化学结构式(Chemical Structure):
参考文献No.7322
标题:2-Pyridyl-penem cpds
作者:Lang, M. (Novartis AG)
来源:EP 0246187; JP 1987263183; US 4826832
合成路线图解说明:

2) The reaction of 3-pyridylcarbonyl chloride (I) with (3S,4R)-2-[3-[1(R)-(allyloxycarbonyloxy)ethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphoranylidene)acetic acid allyl ester silver salt (VII) in dichloromethane containing pyridine gives the substituted phosphorane (VIII), which is cyclized in refluxing toluene to afford (5R,6S)-6-[1(R)-(allyloxycarbonyloxy)ethyl]-2-(3-pyridyl)-2-penem-3-carboxylic acid allyl ester (IX). The deprotection of (IX) with tetrakis(triphenylphosphine)palladium, tributyltin hydride and NaHCO3 in THF gives the free acid (X) as the sodium salt, which is finally esterified with bromomethyl acetate.

参考文献No.358521
标题:TMA-230
作者:Mealy, M.; Casta馿r, J.
来源:Drugs Fut 1996,21(5),493
合成路线图解说明:

1) The reaction of 3-pyridylcarbonyl chloride (I) with (3S,4R)-2-[3-[1(R)-hyroxyethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphoranylidene)acetic acid allyl ester silver salt (II) in dichloromethane containing pyridine gives the substituted phosphorane (III), which is cyclized in refluxing benzene to afford (5R,6S)-6-[1(R)-hydroxyethyl]-2-(3-pyridyl)-2-penem-3-carboxylic acid allyl ester (IV). The deprotection of (IV) by means of triphenylphosphine, tetrakis(triphenylphosphine)palladium and acetic acid yields the free acid (V), which is finally esterified with bromomethyl acetate (VI) in DMF.

合成路线图解说明:

2) The reaction of 3-pyridylcarbonyl chloride (I) with (3S,4R)-2-[3-[1(R)-(allyloxycarbonyloxy)ethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphoranylidene)acetic acid allyl ester silver salt (VII) in dichloromethane containing pyridine gives the substituted phosphorane (VIII), which is cyclized in refluxing toluene to afford (5R,6S)-6-[1(R)-(allyloxycarbonyloxy)ethyl]-2-(3-pyridyl)-2-penem-3-carboxylic acid allyl ester (IX). The deprotection of (IX) with tetrakis(triphenylphosphine)palladium, tributyltin hydride and NaHCO3 in THF gives the free acid (X) as the sodium salt, which is finally esterified with bromomethyl acetate.

参考文献No.366802
标题:Synthesis and structure-activity relations in the class 2-(pyridyl)penems
作者:Bedeschi, A.; Visentin, G.; Perrone, E.; Giudici, F.; Zarini, F.; Franceschi, G.; Meinardi, G.; Castellani, P.; Jabes, D.; Rossi, R.; et al.
来源:J Antibiot 1990,43(3),306-13
合成路线图解说明:

1) The reaction of 3-pyridylcarbonyl chloride (I) with (3S,4R)-2-[3-[1(R)-hyroxyethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphoranylidene)acetic acid allyl ester silver salt (II) in dichloromethane containing pyridine gives the substituted phosphorane (III), which is cyclized in refluxing benzene to afford (5R,6S)-6-[1(R)-hydroxyethyl]-2-(3-pyridyl)-2-penem-3-carboxylic acid allyl ester (IV). The deprotection of (IV) by means of triphenylphosphine, tetrakis(triphenylphosphine)palladium and acetic acid yields the free acid (V), which is finally esterified with bromomethyl acetate (VI) in DMF.

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