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

【结构式】

【分子编号】31980

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

【CA登记号】

【分子式】C₁₅H₂₄O₅

【分子量】284.35256

【元素组成】C 63.36% H 8.51% O 28.13%

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：(IIa)

Reduction of qinghaosu (artemisine) (I) by means of sodium borohydride gives a hemiacetal, artemisininelactol (II). Interaction of the latter compound with methanol in the presence of boron triftuoride gives artemether. It can be prepared even more easily by treating artemisininelactol with methanol in acidic medium. The epimers can be separated by chromatography. However, the product without separation of epimers has been used for clinical studies.

参考文献中间体

合成目标

【1】 The chemistry and synthesis of qinghaosu derivatives. J Tradit Chin Med 1982, 2, 1, 9-16.
【2】 Singh, C.; Tiwari, P.; A one-pot conversion of artemisinin to its ether derivatives. Tetrahedron Lett 2002, 43, 40, 7235.
【3】 Ru-yun, J.; Artemether. Drugs Fut 1982, 7, 10, 716.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IIa)	31980	(1R,4S,5R,8S,9R,10R,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
(IIb)	31981	(1R,4S,5R,8S,9R,10S,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
(IIIa)	31982	methyl (1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-10-yl ether; (1R,4S,5R,8S,9R,10R,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecane		C₁₆H₂₆O₅	详情	详情
(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

Extended Information