ethyl (3aS,4S,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-5-hydroxy-4-[(E)-3-oxo-1-octenyl]octahydro-2-pentalenecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】34343

【品名】ethyl (3aS,4S,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-5-hydroxy-4-[(E)-3-oxo-1-octenyl]octahydro-2-pentalenecarboxylate

【CA登记号】

【分子式】C₂₇H₄₂O₈

【分子量】494.62568

【元素组成】C 65.56% H 8.56% O 25.88%

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：(IX)

The condensation of ethyl bicyclo[4.3.0]nona-3-ene-8-carboxylate (I) with methyl 4-chloroformylbutanoate (II) by means of lithium diisopropylamide in THF yields the ketodiester (III), which is reduced with NaBH4 in methanol to the hydroxydiester (IV). Acetylation of (IV) in the usual way affords the acetate (V), which is submitted to ozonolysis with O3 to give the dialdehyde (VI). The intramolecular aldol condensation of (VI) by means of Zn++ yields the desired hydroxyaldehyde (VII), which is submitted to a Horner-Wittig condensation with 2-oxoheptylidenetributylphosphorane (VIII) affording the enone (IX). The protection of the enone (X) with dihydropyran as usual yields the tetrahydropyranylether (X), which is reduced with NaSH4 in methanol to the unsaturated alcohol (Xl).

参考文献中间体

合成目标

【1】 Sakai, K.; Amemiya, S.; Kojima, K.; A novel synthesis (±)-carbacyclin. Chem Pharm Bull 1984, 32, 4, 1349-54.

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)	34336	ethyl (3aR,7aS)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate		C₁₂H₁₈O₂	详情	详情
(II)	20650	methyl 5-chloro-5-oxopentanoate; methyl-4-chloroformylbutyrate	1501-26-4	C₆H₉ClO₃	详情	详情
(III)	34337	ethyl (3aR,7aS)-2-(5-methoxy-5-oxopentanoyl)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate		C₁₈H₂₆O₅	详情	详情
(IV)	34338	ethyl (3aR,7aS)-2-(1-hydroxy-5-methoxy-5-oxopentyl)-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate		C₁₈H₂₈O₅	详情	详情
(V)	34339	ethyl (3aR,7aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-2,3,3a,4,7,7a-hexahydro-1H-indene-2-carboxylate		C₂₀H₃₀O₆	详情	详情
(VI)	34340	ethyl (3R,4S)-1-[1-(acetoxy)-5-methoxy-5-oxopentyl]-3,4-bis(2-oxoethyl)cyclopentanecarboxylate		C₂₀H₃₀O₈	详情	详情
(VII)	34341	ethyl (3aS,4R,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-4-formyl-5-hydroxyoctahydro-2-pentalenecarboxylate		C₂₀H₃₀O₈	详情	详情
(VIII)	34342	1-(tributylphosphoranylidene)-2-heptanone		C₁₉H₃₉OP	详情	详情
(IX)	34343	ethyl (3aS,4S,5R,6aS)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-5-hydroxy-4-[(E)-3-oxo-1-octenyl]octahydro-2-pentalenecarboxylate		C₂₇H₄₂O₈	详情	详情
(X)	34344	ethyl (3aS,4S,5R,6aR)-2-[1-(acetoxy)-5-methoxy-5-oxopentyl]-4-[(E)-3-oxo-1-octenyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]octahydro-2-pentalenecarboxylate		C₃₃H₅₂O₉	详情	详情

Extended Information