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【结 构 式】 
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【分子编号】33116 【品名】(3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-10-[[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione; (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-10-[[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione 【CA登记号】 |
【 分 子 式 】C45H70ClFN2O13 【 分 子 量 】901.5075832 【元素组成】C 59.95% H 7.83% Cl 3.93% F 2.11% N 3.11% O 23.07% |
合成路线1
该中间体在本合成路线中的序号：(IX)Treatment of (VII) with iodine and sodium acetate under irradiation of a halogen lamp produced N-demethylation to furnish (VIII). Further demethylation of (VIII) to give (IX) was achieved by a similar treatment with iodine and tripotassium phosphate. Finally, reductive condensation of (IX) with cyclopropanecarbaldehyde (X) in the presence of sodium cyanoborohydride yielded the bis(cyclopropylmethyl) derivative.
| 【1】 Randolph, J.; Haviv, F.; Bruncko, M.; Crawford, B.W.; Dalton, C.R.; Frey, L.M.; Kaminski, M.A.; Greer, J.; Sauer, D.R.; Mort, N.A. (Abbott Laboratories Inc.); 3',3'-N-Bis-substd. macrolide LHRH antagonists. US 5972898; WO 9950276 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 33114 | (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-1-(3-chloro-4-fluorophenethyl)-10-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione; (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-1-(3-chloro-4-fluorophenethyl)-10-[[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione | C47H74ClFN2O13 | 详情 | 详情 | |
| (VIII) | 33115 | (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-10-[[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione; (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-10-[[(2S,3R,4S,6R)-3-hydroxy-6-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione | C46H72ClFN2O13 | 详情 | 详情 | |
| (IX) | 33116 | (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-10-[[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione; (3aS,4R,7R,8R,9R,10R,11R,13R,15R,15aR)-10-[[(2S,3R,4S,6R)-4-amino-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-1-(3-chloro-4-fluorophenethyl)-4-ethyl-8-[[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy]-11-methoxy-3a,7,9,11,13,15-hexamethyldecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazole-2,6,14(1H,7H)-trione | C45H70ClFN2O13 | 详情 | 详情 | |
| (X) | 26463 | cyclopropanecarbaldehyde | 1489-69-6 | C4H6O | 详情 | 详情 |