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【结 构 式】 
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【分子编号】14954 【品名】(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-12-[(E)-2-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]-1-methylethenyl]-17-ethyl-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone 【CA登记号】 |
【 分 子 式 】C44H70ClNO11 【 分 子 量 】824.49264 【元素组成】C 64.1% H 8.56% Cl 4.3% N 1.7% O 21.35% |
合成路线1
该中间体在本合成路线中的序号：(IV)The silylation of the known compound FK-520 by means of tert-butyldimethylsilyl chloride (TBDMS-Cl) and imidazole in DMF gives the disilylated compound (II), which is selectively monodesilylated by means of 40% HF in acetonitrile for 2 h at 0 C yielding the monosilylated compound (III). The chlorination of (III) by means of triphenylphosphine in refluxing CCl4 gives the chloro derivative (IV), which is finally desilylated with 40% HF in acetonitrile at room temperature.
| 【1】 Graul, A.; Castaner, J.; SDZ-ASM-981. Drugs Fut 1998, 23, 5, 508. |
| 【2】 Baumann, K.; Emmer, G. (Novartis AG; Novartis Deutschland GmbH); Heteroatoms-containing tricyclic cpds. AU 9165843; EP 0427680; JP 1991223291; US 5352671; US 5912238 . |
| 【3】 Okuhara, M.; Tanaka, H.; Goto, T.; Kino, T.; Hatanaka, H. (Fujisawa Pharmaceutical Co., Ltd.); Tricyclo cpds., a process for their production and pharmaceutical compsn. containing the same. AU 8550596; EP 0184162; JP 1991072483; JP 1991072484; JP 1995224066; JP 1999012281; JP 1999343294; US 4894366; US 4929611; US 4956352; US 5110811; US 5254562; US 5266692; US 5565559 . |
| 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) | 14951 | (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetron | C43H69NO12 | 详情 | 详情 | |
| (II) | 14952 | (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-12-[(E)-2-[(1R,3R,4R)-3,4-dimethoxycyclohexyl]-1-methylethenyl]-17-ethyl-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone | C45H73NO12 | 详情 | 详情 | |
| (III) | 14953 | (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1-hydroxy-12-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone | C44H71NO12 | 详情 | 详情 | |
| (IV) | 14954 | (1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-12-[(E)-2-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]-1-methylethenyl]-17-ethyl-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone | C44H70ClNO11 | 详情 | 详情 |