【结 构 式】 |
【分子编号】58935 【品名】ethyl (2Z)-2-(acetylamino)-2,8-nonadienoate 【CA登记号】 |
【 分 子 式 】C13H21NO3 【 分 子 量 】239.31468 【元素组成】C 65.25% H 8.84% N 5.85% O 20.06% |
合成路线1
该中间体在本合成路线中的序号:(V)The aminoacid building block (VIII) can be prepared by two different ways. The oxidative cleavage of 7-octene-1,2-diol (I) by means of NaIO4 yields aldehyde (II). Partial hydrolysis of diethyl 2-acetamidomalonate (III) provides monoacid (IV), which is subjected to Knoevenagel-type condensation with 6-heptenal (II) in the presence of Ac2O and pyridine to afford enamide (V). Enantioselective hydrogenation of the enamide double bond to the (S)-amidoester (VI) is then achieved by using the Burk's method. In order to replace the N-acetyl protecting group of (VI), the acetamide nitrogen is protected with Boc2O, and the resulting imide (VII) is further hydrolyzed to the target N-Boc aminoacid (VIII) under standard basic conditions.
【1】 Halmos, T.; Llinas-Brunet, M.; Faucher, A.-M.; Ghiro, E.; Goudreau, N.; Tsantrizos, Y.S.; Cameron, D.R. (Boehringer Ingelheim (Canada) Ltd.); Macrocyclic peptides active against the hepatitis C virus. EP 1169339; JP 2002542160; WO 0059929 . |
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) | 58933 | 7-Octene-1,2-diol | C8H16O2 | 详情 | 详情 | |
(II) | 27179 | 6-heptenal | C7H12O | 详情 | 详情 | |
(III) | 16170 | 1,2-dichloroethane | 107-06-2 | C2H4Cl2 | 详情 | 详情 |
(IV) | 58934 | Ethyl 2-acetamidomalonate | C7H11NO5 | 详情 | 详情 | |
(V) | 58935 | ethyl (2Z)-2-(acetylamino)-2,8-nonadienoate | C13H21NO3 | 详情 | 详情 | |
(VI) | 58936 | ethyl (2S)-2-(acetylamino)-8-nonenoate | C13H23NO3 | 详情 | 详情 | |
(VII) | 58937 | (2S)-2-[acetyl(tert-butoxycarbonyl)amino]-8-nonenoic acid | C16H27NO5 | 详情 | 详情 | |
(VIII) | 58938 | (2S)-2-[(tert-butoxycarbonyl)amino]-8-nonenoic acid | C14H25NO4 | 详情 | 详情 |