methyl (Z)-7-[5-oxo-3-([2-[(trimethylsilyl)oxy]ethyl]sulfanyl)-1-cyclopenten-1-yl]-5-heptenoate -Drug Synthesis Database

【结构式】

【分子编号】36378

【品名】methyl (Z)-7-[5-oxo-3-([2-[(trimethylsilyl)oxy]ethyl]sulfanyl)-1-cyclopenten-1-yl]-5-heptenoate

【CA登记号】

【分子式】C₁₈H₃₀O₄SSi

【分子量】370.5853

【元素组成】C 58.34% H 8.16% O 17.27% S 8.65% Si 7.58%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XI)

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.

参考文献中间体

合成目标

【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	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

Extended Information