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【结 构 式】 
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【分子编号】54230 【品名】5,8-Tetradecadienoic acid 【CA登记号】10390-16-6 |
【 分 子 式 】C14H24O2 【 分 子 量 】224.34336 【元素组成】C 74.95% H 10.78% O 14.26% |
合成路线1
该中间体在本合成路线中的序号：(VI)The hydrolysis of the spicamycin mixture (I) with R = alkyl by means of HCl in alcohol or water gives 6-(spicaminylamino)purine (II). (The hydrolysis can also be performed with other inorganic acids such as H2SO4 or organic ones such as acetic acid or formic acid.) The condensation of (II) with N-(tert-butoxycarbonyl)glycine (III) by the active ester method yields the protected glycyl derivative (IV), which is deprotected with TFA (or methanolic HCl) to afford the glycyl derivative (V). Finally, this compound is condensed with tetradeca-2(E),4(E)-dienoic acid (VI) by the active ester method to provide the target carboxamide derivative.
| 【1】 Otake, N.; Kawai, H.; Kawasaki, T.; Odagawa, A.; Kamishohara, M.; Sakai, T. (Kirin Brewery Co., Ltd.); Spicamycin derivs. and the use thereof. EP 0525479; JP 1993186494; US 5461036; US 5631238 . |
| 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) | 54226 | N-(2-{[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]amino}-2-oxoethyl)-14-methylpentadecanamide | n/a | C30H51N7O7 | 详情 | 详情 |
| (II) | 54227 | (2S,3R,4R,5R,6R)-5-amino-6-[(1R)-1,2-dihydroxyethyl]-2-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3,4-diol | n/a | C12H18N6O5 | 详情 | 详情 |
| (III) | 18066 | N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid | 4530-20-5 | C7H13NO4 | 详情 | 详情 |
| (IV) | 54228 | tert-butyl 2-{[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]amino}-2-oxoethylcarbamate | n/a | C19H29N7O8 | 详情 | 详情 |
| (V) | 54229 | 2-amino-N-[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]acetamide | n/a | C14H21N7O6 | 详情 | 详情 |
| (VI) | 54230 | 5,8-Tetradecadienoic acid | 10390-16-6 | C14H24O2 | 详情 | 详情 |