[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl](triphenyl)phosphonium hydrogen sulfate -Drug Synthesis Database

【结构式】

【分子编号】39596

【品名】[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl](triphenyl)phosphonium hydrogen sulfate

【CA登记号】

【分子式】C₃₈H₄₅O₄PS

【分子量】628.812662

【元素组成】C 72.58% H 7.21% O 10.18% P 4.93% S 5.1%

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)

The reduction of retinene (XV) with NaBH4 in methanol gives retinol (XX), which by reaction with triphenylphosphine and H2SO4 is converted into retinyltriphenylphosphonium sulfate (XXI). The Wittig reaction of (XXI) with aldehyde (XVI) by means of sodium methoxide in benzene - methanol yields 3-acetylisocryptoxanthin (XXII), which by reaction with aqueous 68% HBr in methylene chloride, followed by a treatment with Na2CO3 affords dehydro-retro-carotene (XXIII).

参考文献中间体

合成目标

【1】 Surmatis, J.D.; et al.; Synthesis of oxygenated carotenoids. Helv Chim Acta 1970, 53, 5, 974-990.
【2】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Canthazanthin. Drugs Fut 1979, 4, 7, 477.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XV)	39590	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal		C₂₀H₂₈O	详情	详情
(XVI)	39591	3-[(1E,3E,5E,7E)-3,7-dimethyl-9-oxo-1,3,5,7-nonatetraenyl]-2,4,4-trimethyl-2-cyclohexen-1-yl acetate		C₂₂H₃₀O₃	详情	详情
(XX)	39595	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol	68-26-8	C₂₀H₃₀O	详情	详情
(XXI)	39596	[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenyl](triphenyl)phosphonium hydrogen sulfate		C₃₈H₄₅O₄PS	详情	详情
(XXII)	39597	2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,5,7,9,11,13,15,17-octadecanonaenyl]-2-cyclohexen-1-yl acetate		C₄₂H₅₈O₂	详情	详情
(XXIII)	39598	1,5,5-trimethyl-6-[(Z,2E,4E,6E,8E,10E,12E,14E,16E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-2,4,6,8,10,12,14,16-octadecaoctaenylidene]-1-cyclohexene		C₄₀H₅₄	详情	详情

Extended Information