(1R,4S,5R,8S,9R,10R,12S,13R)-10-fluoro-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane -Drug Synthesis Database

【结构式】

【分子编号】22371

【品名】(1R,4S,5R,8S,9R,10R,12S,13R)-10-fluoro-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane

【CA登记号】

【分子式】C₁₅H₂₃FO₄

【分子量】286.3436232

【元素组成】C 62.92% H 8.1% F 6.63% O 22.35%

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：(III)

Artemisinin (I) was reduced to the dihydro analogue (II), and subsequently the 10-hydroxyl group was substituted for a fluorine atom using diethylaminosulfur trifluoride. The desired 10-beta-isomer (III) was then separated by column chromatography. Finally, boron trifluoride-promoted Friedel Crafts condensation with furan (IV) at low temperature provided the target furyl compound, the major 10-beta isomer being isolated by chromatography on Florisil.

参考文献中间体

合成目标

【1】 Posner, G.H.; Parker, M.H.; Northrop, J.; Elias, J.S.; Ploypradith, P.; Xie, S.; Shapiro, T.A.; Orally active, hydrolytically stable, semisynthetic, antimalarial trioxanes in the artemisinin family. J Med Chem 1999, 42, 2, 300.

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)	22369	Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one	63968-64-9	C₁₅H₂₂O₅	详情	详情
(II)	22370	Dihydroartemisinin; (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-ol		C₁₅H₂₄O₅	详情	详情
(III)	22371	(1R,4S,5R,8S,9R,10R,12S,13R)-10-fluoro-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane		C₁₅H₂₃FO₄	详情	详情
(IV)	22372	Furan	110-00-9	C₄H₄O	详情	详情

Extended Information