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【结 构 式】 
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【分子编号】12681 【品名】(3S,4R)-2-[3-[1(R)-(Allyloxycarbonyloxy)ethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphanylidene)acetic acid allyl ester S-silver salt 【CA登记号】 |
【 分 子 式 】C32H31AgNO6PS 【 分 子 量 】696.509242 【元素组成】C 55.18% H 4.49% Ag 15.49% N 2.01% O 13.78% P 4.45% S 4.6% |
合成路线1
该中间体在本合成路线中的序号：(VII)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.
| 【1】 Mealy, M.; Castaner, J.; TMA-230. Drugs Fut 1996, 21, 5, 493. |
| 【2】 Lang, M. (Novartis AG); 2-Pyridyl-penem cpds. EP 0246187; JP 1987263183; US 4826832 . |
| 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 | |
| (VI) | 12680 | bromomethyl acetate | 590-97-6 | C3H5BrO2 | 详情 | 详情 |
| (VII) | 12681 | (3S,4R)-2-[3-[1(R)-(Allyloxycarbonyloxy)ethyl]-2-oxo-4-sulfanylazetidin-1-yl]-2-(triphenylphosphanylidene)acetic acid allyl ester S-silver salt | C32H31AgNO6PS | 详情 | 详情 | |
| (VIII) | 12682 | allyl 2-[(3S,4R)-3-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-2-oxo-4-[(3-pyridinylcarbonyl)sulfanyl]azetidinyl]-2-(triphenylphosphoranylidene)acetate | C38H35N2O7PS | 详情 | 详情 | |
| (IX) | 12683 | allyl (5R,6S)-6-((1R)-1-[[(allyloxy)carbonyl]oxy]ethyl)-7-oxo-3-(3-pyridinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C20H20N2O6S | 详情 | 详情 | |
| (X) | 12684 | sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(3-pyridinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | C13H11N2NaO4S | 详情 | 详情 |