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【结 构 式】 
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【分子编号】63846 【品名】(3S,4S,5S,10S,10aS)-5-{(3S,4S,7S)-10-hydroxy-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,7,8-tetrahydro-1H-benzo[g]isochromen-5-yl}-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,4a,5,10,10a-hexahydro-1H-benzo[g]isochromen-10-ol 【CA登记号】 |
【 分 子 式 】C36H48O14 【 分 子 量 】704.76872 【元素组成】C 61.35% H 6.86% O 31.78% |
合成路线1
该中间体在本合成路线中的序号：(XII)Bisnaphthol (XI) was chromatographically separated into atropisomers (XII) and (XIII). The required isomer (XII) was benzylated with NaH and benzyl bromide, and the methoxymethyl group was removed by treatment with HCl, generated from acetyl chloride in MeOH, to furnish diol (XIV). Reduction of one hydroxyl group of (XIV) was then effected by the sequence of conversion to the S-methyl dithiocarbonate (XV), followed by radical deoxygenation with n-Bu3SnH and AIBN to yield (XVI). The O-benzyl groups of (XVI) were finally removed by hydrogenation over Pd/C.
| 【1】 Yamazaki, T.; Yoshimoto, T.; Tatsuta, K.; Synthesis and biological evaluation of the analogs of bioxanthracenes ES-242s, N-methyl-D-aspartate antagonists. J Antibiot 1998, 51, 3, 383. |
| 【2】 Yamazaki, T.; Nagai, T.; Tamura, T.; Tatsuta, K.; Mase, T.; Synthesis of an N-methyl-D-aspartate receptor antagonist, ES-242-5, and its analogs. J Antibiot 1999, 52, 4, 422. |
| 【3】 Nakamura, H.; Absolute and atropisomeric structure of ES-242s, N-methyl-D-aspartate receptor antagonists. J Antibiot 1999, 52, 4, 433. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 31519 | 5,5'-Bis[7,9-dimethoxy-4(S)-(methoxymethoxy)-3(S)-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-10-ol] | C36H42O12 | 详情 | 详情 | |
| (XII) | 63846 | (3S,4S,5S,10S,10aS)-5-{(3S,4S,7S)-10-hydroxy-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,7,8-tetrahydro-1H-benzo[g]isochromen-5-yl}-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,4a,5,10,10a-hexahydro-1H-benzo[g]isochromen-10-ol | C36H48O14 | 详情 | 详情 | |
| (XIII) | 63847 | (3S,4S,5R,10R,10aR)-5-{(3S,4S,7R)-10-hydroxy-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,7,8-tetrahydro-1H-benzo[g]isochromen-5-yl}-7,9-dimethoxy-3-methyl-4-[(methylperoxy)methoxy]-3,4,4a,5,10,10a-hexahydro-1H-benzo[g]isochromen-10-ol | C36H48O14 | 详情 | 详情 | |
| (XIV) | 31522 | (3S,4S)-10-(benzyloxy)-5-[(3S,4S)-10-(benzyloxy)-4-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-4-ol | C46H46O10 | 详情 | 详情 | |
| (XV) | 31523 | O-[(3S,4S)-10-(benzyloxy)-5-[(3S,4S)-10-(benzyloxy)-4-hydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-4-yl] S-methyl carbonodithioate | C48H48O10S2 | 详情 | 详情 | |
| (XVI) | 31524 | (3S,4S)-10-(benzyloxy)-5-[(3S)-10-(benzyloxy)-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-4-ol | C46H46O9 | 详情 | 详情 |