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【结 构 式】 
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【分子编号】36377 【品名】1-[[[(E)-3-iodo-1-pentyl-2-propenyl]oxy](diphenyl)methyl]benzene; (E)-3-iodo-1-pentyl-2-propenyl trityl ether 【CA登记号】 |
【 分 子 式 】C27H29IO 【 分 子 量 】496.43113 【元素组成】C 65.33% H 5.89% I 25.56% O 3.22% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)The protection of the free hydroxy group of (X) with trimethylchlorosilane and hexamethyldisilazane in pyridine gives the trimethylsilyl derivative (XI), which is condensed with [3-(triphenylmethoxy)-1-octenyl](pentenyl)lithiocuprate (XII) in HMPT-ether to afford 11-deoxy-11alpha-(2-trimethyl-silyloxyethylthio)-15-triphenylmethoxy-PGE2 methyl ester (XIII). Finally, this compound is deprotected by treatment with acetic acid in THF. The lithium cuprate (XII) is prepared as follows: Hydrogen iodide addition to 3-triphenylmethoxy-1-octyne (XVII) gives 1-iodo-3-triphenylmethoxy-1-octene (XVIII), which is condensed with copper 1-pentyne (B) and butyllithium in ether.
| 【1】 Floyd, M.; et al.; Prostaglandins and congeners. 22. Synthesis of 11-substituted derivatives of 11-deoxyprostaglandins E1 and E2. Potential bronchodilators. J Med Chem 1980, 23, 8, 903-913. |
| 【2】 Hillier, K.; Serradell, M.N.; Blancafort, P.; Castañer, J.; DHET-PGE2. Drugs Fut 1982, 7, 4, 241. |
| 【3】 Weiss, M.J.; Siuta, G.J. (American Cyanamid Co.); 11-(2-Hydroxyethylthio)prostenoic acid E{HD 2 {B series derivatives. US 4085272 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 29069 | 1-pentynylcopper | C5H7Cu | 详情 | 详情 | |
| (X) | 36371 | methyl (Z)-7-[3-[(2-hydroxyethyl)sulfanyl]-5-oxo-1-cyclopenten-1-yl]-5-heptenoate | C15H22O4S | 详情 | 详情 | |
| (XI) | 36378 | methyl (Z)-7-[5-oxo-3-([2-[(trimethylsilyl)oxy]ethyl]sulfanyl)-1-cyclopenten-1-yl]-5-heptenoate | C18H30O4SSi | 详情 | 详情 | |
| (XII) | 36379 | C32H37IO | 详情 | 详情 | ||
| (XIII) | 36380 | methyl (Z)-7-[(1R,2R,3R)-5-oxo-3-([2-[(trimethylsilyl)oxy]ethyl]sulfanyl)-2-[(E,3S)-3-(trityloxy)-1-octenyl]cyclopentyl]-5-heptenoate | C45H60O5SSi | 详情 | 详情 | |
| (XVII) | 36376 | 1-pentyl-2-propynyl trityl ether; 1-[[(1-pentyl-2-propynyl)oxy](diphenyl)methyl]benzene | C27H28O | 详情 | 详情 | |
| (XVIII) | 36377 | 1-[[[(E)-3-iodo-1-pentyl-2-propenyl]oxy](diphenyl)methyl]benzene; (E)-3-iodo-1-pentyl-2-propenyl trityl ether | C27H29IO | 详情 | 详情 |