3-[(4R,5S)-5-hexyl-2,2,5-trimethyl-1,3-dioxolan-4-yl]-5-hydroxy-5-isopropyl-2(5H)-furanone -Drug Synthesis Database

【结构式】

【分子编号】26148

【品名】3-[(4R,5S)-5-hexyl-2,2,5-trimethyl-1,3-dioxolan-4-yl]-5-hydroxy-5-isopropyl-2(5H)-furanone

【CA登记号】

【分子式】C₁₉H₃₂O₅

【分子量】340.46008

【元素组成】C 67.03% H 9.47% O 23.5%

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：(XVIII)

Photochemical singlet oxygen addition to the silyl furan (XVII) in the presence of the sensitizer rose Bengal under irradiation of a mercury lamp afforded lactone (XVIII). The isopropylidene ketal of (XVIII) was then hydrolyzed to give glycol (XIX). Methyl acetalization of the hemiacetal hydroxyl group of (XIX) with dimethyl sulfate under basic conditions provided (XX). This was treated with liquid ammonia in MeOH to obtain the desired gamma-lactam (XXI) together with a small amount of lactone (XIX) that was separated by column chromatography. Methyl acetal reintroduction in (XXI) with MeOH in the presence of camphorsulfonic acid gave (XXII). Finally, oxidation of the secondary hydroxyl of (XXII) group with Dess-Martin periodinane furnished the title compound, existing as a 1:1 mixture of diastereomeric acetals.

参考文献中间体

合成目标

【1】 Shiraki, R.; et al.; Total synthesis of PI-091. Tetrahedron Lett 1995, 36, 31, 5551.
【2】 Shiraki, R.; et al.; Total synthesis of natural PI-091, a new platelet aggregation inhibitor of microbial origin. J Org Chem 1996, 61, 8, 2845.

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)	18845	Dess-Martin periodinane; 1,1,1-Triacetoxy-1,2-benziodoxol-3(1H)-one	87413-09-0	C₁₃H₁₃IO₈	详情	详情
(XVII)	26147	[3-[(4R,5S)-5-hexyl-2,2,5-trimethyl-1,3-dioxolan-4-yl]-5-isopropyl-2-furyl](trimethyl)silane		C₂₂H₄₀O₃Si	详情	详情
(XVIII)	26148	3-[(4R,5S)-5-hexyl-2,2,5-trimethyl-1,3-dioxolan-4-yl]-5-hydroxy-5-isopropyl-2(5H)-furanone		C₁₉H₃₂O₅	详情	详情
(XIX)	26149	3-[(1R,2S)-1,2-dihydroxy-2-methyloctyl]-5-hydroxy-5-isopropyl-2(5H)-furanone		C₁₆H₂₈O₅	详情	详情
(XX)	26150	3-[(1R,2S)-1,2-dihydroxy-2-methyloctyl]-5-isopropyl-5-methoxy-2(5H)-furanone		C₁₇H₃₀O₅	详情	详情
(XXI)	26151	3-[(1R,2S)-1,2-dihydroxy-2-methyloctyl]-5-hydroxy-5-isopropyl-1,5-dihydro-2H-pyrrol-2-one		C₁₆H₂₉NO₄	详情	详情
(XXII)	26152	3-[(1R,2S)-1,2-dihydroxy-2-methyloctyl]-5-isopropyl-1,5-dihydro-2H-pyrrol-2-one		C₁₆H₂₉NO₃	详情	详情

Extended Information