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【结 构 式】

【分子编号】37114

【品名】methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4S)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate

【CA登记号】

【 分 子 式 】C26H41IO7

【 分 子 量 】592.51181

【元素组成】C 52.71% H 6.97% I 21.42% O 18.9%

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:(IIIa)

16-Methylprostaglandin PGF2alpha methyl ester (Ia-b) is cyclized with iodine/sodium bicarbonate to give (IIa-b), which is acetylated with acetic anhydride/pyridine to (IIIa-b). Dehydrohalogenation with DBN generates the protected PGI2 analogue (IVa-b), which reacts smoothly with chlorosulfonyl isocyanate (A) to afford the adduct (Va-b). Without isolation (Va-b) gives on treatment with triethylamine in acetonitrile or solvolysis with N,N-dimethylformamide (DMF) the stable protected 5-cyano analoque (VIa-b), which contains up to ca. 5% Z-isomer, readily removed by chromatography. Finally, saponification affords the free ZK-34,798 (nileprost).

1 Lohaus, G.; Nitrilsynthesen mit chlorsulfonylisocyanat. Chem Ber 1967, 100, 2719-29.
2 Vorbruggen, H.; Reaktive isocyanate I. Sie direkte einfuehrung von nitrilgruppen in ungesattigte systeme. Eine einfache umwandlung von carbosauren in ihre nitrile. Tetrahedron Lett 1968, 1631-34.
3 Tanouchi, T.; Miyake, H.; Igushi, Y.; Hayashi, M.; Iguchi, S.; The synthesis of 16(R)- or 16(S)-methylprostaglandins. J Org Chem 1973, 38, 1250-51.
4 Whittaker, N.; A synthesis of prostaglandin sodium salt. Tetrahedron Lett 1977, 2805-08.
5 Vorbruggen, H.; Skuballa, W.; Raduchel, B.; Losert, W.; Loge, P.; Muller, B.; Mannesmann, G. (Schering AG); 5-Cyano-prostacyclin derivs.. US 4219479 .
6 Hashimoto, S.; Nileprost. Drugs Fut 1982, 7, 9, 643.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 14101 Chlorosulfonyl isocyanate 1189-71-5 CClNO3S 详情 详情
(Ia) 37110 methyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R,4S)-3-hydroxy-4-methyloctyl]cyclopentyl]-5-heptenoate C22H40O5 详情 详情
(Ib) 37111 methyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R,4R)-3-hydroxy-4-methyloctyl]cyclopentyl]-5-heptenoate C22H40O5 详情 详情
(IIa) 37112 methyl 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S,4S)-3-hydroxy-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C22H37IO5 详情 详情
(IIb) 37113 methyl 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S,4R)-3-hydroxy-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C22H37IO5 详情 详情
(IIIa) 37114 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4S)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C26H41IO7 详情 详情
(IIIb) 37115 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4R)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-yl]-5-iodopentanoate C26H41IO7 详情 详情
(IVa) 37116 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4S)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoate C26H40O7 详情 详情
(IVb) 37117 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4R)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoate C26H40O7 详情 详情
(Va) 37118 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4S)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]-6-[(chlorosulfonyl)amino]-6-oxohexanoate C27H40ClNO10S 详情 详情
(Vb) 37119 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4R)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]-6-[(chlorosulfonyl)amino]-6-oxohexanoate C27H40ClNO10S 详情 详情
(VIa) 37120 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4S)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]-5-cyanopentanoate C27H39NO7 详情 详情
(VIb) 37121 methyl 5-[(3aR,4R,5R,6aS)-5-(acetoxy)-4-[(E,3S,4R)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-ylidene]-5-cyanopentanoate C27H39NO7 详情 详情
Extended Information