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【结 构 式】 
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【分子编号】52650 【品名】4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoic acid 【CA登记号】 |
【 分 子 式 】C18H21O6P 【 分 子 量 】364.334902 【元素组成】C 59.34% H 5.81% O 26.35% P 8.5% |
合成路线1
该中间体在本合成路线中的序号：(V)The esterification of sodium 4-hydroxybutyrate (I) with 4-nitrobenzyl chloride (II) gives the corresponding ester (III), which is condensed with dibenzyl chlorophosphate (III) in pyridine, yielding the expected phosphoric ester (IV). The cleavage of the 4-nitrobenzyl ester of (IV) with Na2S or Zn/HCl affords the butyric acid derivative (V), which is condensed with SCH-56592 (VI) by means of DMAP and Ts-Cl to provide the corresponding ester (VII). Finally, the benzyl groups of the phosphate moiety of (VII) are cleaved by hydrogenation with H2 or HCOOH over Pd/C in THF, giving rise to the target SCH-59884.
| 【1】 Lee, G.M.; et al.; Synthesis of injectable antifungal Sch 59884. Org Process Res Dev 2001, 5, 6, 622. |
| 【2】 Lee, G.M.; et al.; Synthesis of injectable antifungal Sch 59884. (Erratum). Org Process Res Dev 2002, 6, 1, 86. |
| 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) | 34856 | sodium 4-hydroxybutanoate | 502-85-2 | C4H7NaO3 | 详情 | 详情 |
| (II) | 52647 | (4-nitrophenyl)methyl 4-hydroxybutanoate | C11H13NO5 | 详情 | 详情 | |
| (III) | 52648 | Chlorophosphoric acid dibenzyl ester; Dibenzylphosphoryl chloride | 538-37-4 | C14H14ClO3P | 详情 | 详情 |
| (IV) | 52649 | (4-nitrophenyl)methyl 4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoate | C25H26NO8P | 详情 | 详情 | |
| (V) | 52650 | 4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoic acid | C18H21O6P | 详情 | 详情 | |
| (VI) | 52651 | 1-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-3-(1-ethyl-2-hydroxypropyl)-1,3-dihydro-2H-imidazol-2-one | C38H43F2N7O4 | 详情 | 详情 | |
| (VII) | 52652 | 2-[3-(4-{4-[4-({[5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl}oxy)phenyl]-1-piperazinyl}phenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-1-methylbutyl 4-({bis[(phenylmethyl)oxy]phosphoryl}oxy)butanoate | C56H62F2N7O9P | 详情 | 详情 |