(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol -Drug Synthesis Database

【结构式】

【分子编号】34476

【品名】(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol

【CA登记号】

【分子式】C₂₀H₃₄O

【分子量】290.48936

【元素组成】C 82.69% H 11.8% O 5.51%

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：(I)

Mitsunobu coupling of geranylgeraniol (I) with N-hydroxyphthalimide (II) in the presence of diethyl azodicarboxylate and triphenylphosphine produced the N-alkoxyphthalimide (III). Subsequent hydrazinolysis of the phthaloyl group of (III) gave rise to the O-alkyl hydroxylamine (IV). (2-Diethylphosphono)butyric acid (VI), prepared by partial hydrolysis of triethyl ester (V), was then coupled with hydroxylamine (IV) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide-HCl and 1-hydroxybenzotriazole to furnish the N-alkoxyamide (VII). The phosphonate ester groups were finally cleaved by treatment with bromotrimethylsilane and 2,4,6-collidine.

参考文献中间体

合成目标

【1】 Balsamo, A.; Macchia, B.; Macchia, M.; Baldacci, M.; Danesi, R.; Del Tacca, M. (Laboratori Baldacci SpA); Novel geranylgeranyl-derivs., process for the preparation thereof and related pharmaceutical compsns.. EP 0862575; JP 2000500758; WO 9719091 .

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)	34476	(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol		C₂₀H₃₄O	详情	详情
(II)	13505	N-Hydroxyphthalimide; 2-Hydroxy-1H-isoindole-1,3(2H)-dione	524-38-9	C₈H₅NO₃	详情	详情
(III)	34477	2-[[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]oxy]-1H-isoindole-1,3(2H)-dione		C₂₈H₃₇NO₃	详情	详情
(IV)	34478	O-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]hydroxylamine; (2E,6E,10E)-1-(aminooxy)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene		C₂₀H₃₅NO	详情	详情
(V)	20274	ethyl 2-(diethoxyphosphoryl)butanoate	17145-91-4	C₁₀H₂₁O₅P	详情	详情
(VI)	34479	2-(diethoxyphosphoryl)butyric acid		C₈H₁₇O₅P	详情	详情
(VII)	34480	diethyl 1-[([[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]oxy]amino)carbonyl]propylphosphonate		C₂₈H₅₀NO₅P	详情	详情

Extended Information