【结 构 式】 |
【分子编号】34479 【品名】2-(diethoxyphosphoryl)butyric acid 【CA登记号】 |
【 分 子 式 】C8H17O5P 【 分 子 量 】224.193742 【元素组成】C 42.86% H 7.64% O 35.68% P 13.82% |
合成路线1
该中间体在本合成路线中的序号:(VI)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.
【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 |