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【结 构 式】 
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【分子编号】24176 【品名】methyl (2R)-2-(acetamido)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate 【CA登记号】 |
【 分 子 式 】C16H21NO5 【 分 子 量 】307.34648 【元素组成】C 62.53% H 6.89% N 4.56% O 26.03% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Synthesis of intermediate (VI): 2) The reaction of 5,8-dimethoxy-2-tetralone (I) with KCN and ammonium carbonate in refluxing ethanol gives 2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid (II), which is acetilated with acetic anhydride to give 2-acetylamino-1,2,3,4-tetrahydro-2-naphthoic acid (XV), which is submitted to optical resolution with I-alpha-phenylethylamine yielding the 2(R) isomer (XVI). Esterification of (XVI) with methanol-H2SO4 affords the corresponding methyl ester (XVII), which by reaction first with NaH and DMSO and then with Al-Hg in THF is converted into the acetyl derivative (VI).
| 【1】 Ishizumi, K.; Ohashi, N.; Tanno, N.; Sato, H.; Fukui, M.; Morisada, S. (Sumitomo Pharmaceuticals Co., Ltd.); Aminonaphthacene derivs.. EP 0107486; US 4673668 . |
| 【2】 Hoshi, A.; Prous, J.; Castaner, J.; SM-5887. Drugs Fut 1988, 13, 11, 962. |
| 【3】 Ishizumi, K.; et al.; Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-Amino-9-deoxydaunomycin and related compounds. J Org Chem 1987, 52, 20, 4477-85. |
| 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) | 24172 | 5,8-dimethoxy-3,4-dihydro-2(1H)-naphthalenone | C12H14O3 | 详情 | 详情 | |
| (II) | 24173 | 2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid | C13H17NO4 | 详情 | 详情 | |
| (VI) | 24175 | N-[(2R)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl]acetamide | C16H21NO4 | 详情 | 详情 | |
| (XV) | 24174 | 2-(acetamido)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid | C15H19NO5 | 详情 | 详情 | |
| (XVI) | 24177 | (2R)-2-(acetamido)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid | C15H19NO5 | 详情 | 详情 | |
| (XVII) | 24176 | methyl (2R)-2-(acetamido)-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate | C16H21NO5 | 详情 | 详情 |