(1S,4S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-17-oxo-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-4-yl myristate -Drug Synthesis Database

【结构式】

【分子编号】30294

【品名】(1S,4S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-17-oxo-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-4-yl myristate

【CA登记号】

【分子式】C₅₃H₇₀O₇Si

【分子量】847.2201

【元素组成】C 75.14% H 8.33% O 13.22% Si 3.32%

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：(XXI)

Ketone (XVI) was treated with phenylselanyl chloride and LHMDS yielding the selenium derivative (XVII). Enone (XVIII) was then produced by oxidative elimination of the selenide (XVII). Reduction of the unsaturated ketone (XVIII) with NaBH4 in the presence of CeCl3 gave the 3-beta-allylic alcohol (XIX). This was acylated with myristoyl chloride (XX) to afford ester (XXI). Finally, acid deprotection of the silyl ether and the p-methoxyphenyl acetal of (XXI) furnished the title compound.

参考文献中间体

合成目标

【1】 Winkler, J.D.; Lewin, N.E.; Blumberg, P.M.; Harrison, S.; Kim, S.; Synthesis and biological evaluation of highly functionalized analogues of ingenol. J Am Chem Soc 1999, 121, 2, 296.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVI)	30290	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadec-10-ene-4,17-dione		C₃₉H₄₄O₆Si	详情	详情
(XVII)	30291	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-3-(phenylselanyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadec-10-ene-4,17-dione		C₄₅H₄₈O₆SeSi	详情	详情
(XVIII)	30292	(1S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-diene-4,17-dione		C₃₉H₄₂O₆Si	详情	详情
(XIX)	30293	(1S,4S,5R,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-4-hydroxy-7-(4-methoxyphenyl)-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-17-one		C₃₉H₄₄O₆Si	详情	详情
(XX)	30295	tetradecanoyl chloride	112-64-1	C₁₄H₂₇ClO	详情	详情
(XXI)	30294	(1S,4S,5S,7R,9R,12R)-10-([[tert-butyl(diphenyl)silyl]oxy]methyl)-7-(4-methoxyphenyl)-17-oxo-6,8-dioxatetracyclo[10.4.1.0(1,5).0(5,9)]heptadeca-2,10-dien-4-yl myristate		C₅₃H₇₀O₇Si	详情	详情

Extended Information