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【结 构 式】 
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【分子编号】58523 【品名】(7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18-hexamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.1~4,7~.0~5,36~.0~26,35~.0~28,33~]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate 【CA登记号】 |
【 分 子 式 】C42H46N2O13 【 分 子 量 】786.83292 【元素组成】C 64.11% H 5.89% N 3.56% O 26.43% |
合成路线1
该中间体在本合成路线中的序号：(III)The benzoxazinorifamycin (III) was obtained by oxidative condensation of rifamycin S (I) with 2-aminoresorcinol (II). 1-Isobutylpiperazine (V), prepared by alkylation of piperazine (IV) with isobutyl bromide, was then coupled to the benzoxazine ring of (III) in the presence of MnO2 as the oxidant to afford the target piperazinyl derivative. In an improved procedure, 2-aminoresorcinol (II) was protected as the mono-silyl ether (VI) and subsequently coupled to rifamycin S (I) in the presence of MnO2, yielding (VII). Oxidative coupling of the benzoxazino derivative (VII) with 1-isobutylpiperazine (V) proceeded with simultaneous desilylation to furnish the title compound.
| 【1】 Yamane, T.; Hashizume, T.; Yamashita, K.; Hosoe, K.; Kuze, F.; Watanabe, K. (Kaneka Corp.); 3'-Hydroxybenzoxazinorifamycin deriv., process for preparing the same and antibacterial agent containing them. EP 0366914; JP 1991007291; US 4983602 . |
| 【2】 Yamane, T.; et al.; Synthesis and biological activity of 3'-hydroxy-5'-aminobenzoxazinorifamycin derivatives. Chem Pharm Bull 1993, 41, 1, 148. |
| 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) | 58522 | (7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18-hexamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1~4,7~.0~5,28~]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate | C36H43NO12 | 详情 | 详情 | |
| (II) | 58101 | 2-amino-1,3-benzenediol | C6H7NO2 | 详情 | 详情 | |
| (III) | 58523 | (7S,11S,12R,13S,14R,15R,16R,17S,18S)-2,15,17,32-tetrahydroxy-11-methoxy-3,7,12,14,16,18-hexamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.1~4,7~.0~5,36~.0~26,35~.0~28,33~]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate | C42H46N2O13 | 详情 | 详情 | |
| (IV) | 10355 | Diethylenediamine; Piperazine | 110-85-0 | C4H10N2 | 详情 | 详情 |
| (V) | 58524 | N-Isobutyl piperazine | 5308-28-1 | C8H18N2 | 详情 | 详情 |
| (VI) | 58102 | 2-amino-3-{[tert-butyl(dimethyl)silyl]oxy}phenol | C12H21NO2Si | 详情 | 详情 | |
| (VII) | 58525 | (7S,11S,12R,13S,14R,15R,16R,17S,18S)-32-{[tert-butyl(dimethyl)silyl]oxy}-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18-hexamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11.1.1~4,7~.0~5,36~.0~26,35~.0~28,33~]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate | C48H60N2O13Si | 详情 | 详情 |