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【结 构 式】 
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【分子编号】12677 【品名】allyl 2-[(3S,4R)-3-[(1R)-1-hydroxyethyl]-2-oxo-4-[(3-pyridinylcarbonyl)sulfanyl]azetidinyl]-2-(triphenylphosphoranylidene)acetate 【CA登记号】 |
【 分 子 式 】C34H31N2O5PS 【 分 子 量 】610.670382 【元素组成】C 66.87% H 5.12% N 4.59% O 13.1% P 5.07% S 5.25% |
合成路线1
该中间体在本合成路线中的序号：(III)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.
| 【1】 Mealy, M.; Castaner, J.; TMA-230. Drugs Fut 1996, 21, 5, 493. |
| 【2】 Bedeschi, A.; Visentin, G.; Perrone, E.; et al.; Synthesis and structure-activity relations in the class 2-(pyridyl)penems. J Antibiot 1990, 43, 3, 306-13. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10753 | Nicotinoyl chloride | C6H4ClNO | 详情 | 详情 | |
| (II) | 12676 | (3S,4R)-2-[3-(1(R)-Hydroxyethyl)-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphanylidene)acetic acid allyl ester S-silver salt | C28H27AgNO4PS | 详情 | 详情 | |
| (III) | 12677 | allyl 2-[(3S,4R)-3-[(1R)-1-hydroxyethyl]-2-oxo-4-[(3-pyridinylcarbonyl)sulfanyl]azetidinyl]-2-(triphenylphosphoranylidene)acetate | C34H31N2O5PS | 详情 | 详情 | |
| (IV) | 12678 | allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(3-pyridinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C16H16N2O4S | 详情 | 详情 | |
| (V) | 12679 | (5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-(3-pyridinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | C13H12N2O4S | 详情 | 详情 | |
| (VI) | 12680 | bromomethyl acetate | 590-97-6 | C3H5BrO2 | 详情 | 详情 |