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【结 构 式】 
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【分子编号】50189 【品名】methyl (3R)-3-aminohexadecanoate 【CA登记号】 |
【 分 子 式 】C17H35NO2 【 分 子 量 】285.47044 【元素组成】C 71.53% H 12.36% N 4.91% O 11.21% |
合成路线1
该中间体在本合成路线中的序号：(VI)Wittig reaction between aldehyde (I) and methyl(triphenylphosphoranylidene triphenyl)-acetate (II) in refluxing toluene provides E-olefin (III), which is then subjected to reaction with lithium derivative (IV) in THF to afford adduct (V). Benzyl groups of (V) are removed by hydrogenation over Pd(OH)2 in HOAc:MeOH:EtOAc to furnish amine (VI), which is then coupled to Z-Orn(Boc)-OH using 1-ethyl-3-dimethylaminopropylcarbodiimide (WSCD.HCl) and HOBt in CH2Cl2 to give beta-amino acid derivative (VIII). Saponification of the methyl ester group in (VIII) by means of LiOH, followed by condensation with HOBt by means of WSCD.HCl, yields activated ester (IX).
| 【1】 Hashimoto, S.; Hashimoto, M.; Tanaka, A.; Fujie, A.; Shigematsu, N.; Barrett, D.; An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469. Tetrahedron Lett 2001, 42, 4, 703. |
| 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) | 50186 | Myristaldehyde; Myristyl aldehyde; Tetradecanal; Myristic aldehyde trimer; Tetradecyl aldehyde | 124-25-4 | C14H28O | 详情 | 详情 |
| (II) | 14689 | Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate | 2605-67-6 | C21H19O2P | 详情 | 详情 |
| (III) | 50187 | methyl (E)-2-hexadecenoate | C17H32O2 | 详情 | 详情 | |
| (IV) | 30864 | N-Benzyl-N-(1(R)-phenylethyl)amide lithium salt | C15H16LiN | 详情 | 详情 | |
| (V) | 50188 | methyl (3R)-3-[benzyl[(1R)-1-phenylethyl]amino]hexadecanoate | C32H49NO2 | 详情 | 详情 | |
| (VI) | 50189 | methyl (3R)-3-aminohexadecanoate | C17H35NO2 | 详情 | 详情 | |
| (VII) | 50190 | (2S)-2-[[(benzyloxy)carbonyl]amino]-5-[(tert-butoxycarbonyl)amino]pentanoic acid | C18H26N2O6 | 详情 | 详情 | |
| (VIII) | 50191 | methyl (3R)-3-([(2S)-2-[[(benzyloxy)carbonyl]amino]-5-[(tert-butoxycarbonyl)amino]pentanoyl]amino)hexadecanoate | C35H59N3O7 | 详情 | 详情 | |
| (IX) | 50192 | tert-butyl (4S)-5-([(1R)-1-[2-(1H-1,2,3-benzotriazol-1-yloxy)-2-oxoethyl]tetradecyl]amino)-4-[[(benzyloxy)carbonyl]amino]-5-oxopentylcarbamate | C40H60N6O7 | 详情 | 详情 |