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【结 构 式】 
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【分子编号】32995 【品名】[(2S,5S)-5-ethynyltetrahydro-2-furanyl]methyl 4-fluorophenyl ether; (2S,5S)-2-ethynyl-5-[(4-fluorophenoxy)methyl]tetrahydrofuran 【CA登记号】 |
【 分 子 式 】C13H13FO2 【 分 子 量 】220.2434232 【元素组成】C 70.9% H 5.95% F 8.63% O 14.53% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Intermediate (XVI) is treated with BuLi and diisopropylamine in THF giving the chiral acetylenic tetrahydrofuran (XVII). The addition of ethylene oxide (XVIII) to the terminal acetylene of (XVII) by means of BF3/Et2O in THF gives the 3-butyl-1-ol derivative (XIX), which is condensed with N,O-bis(phenoxy- carbonyl)hydroxylamine (XX) by means of PPh3 and diisopropylazodicarboxylate (DIAD) in THF yielding the final intermediate (XXI). Finally, this compound is treated with ammonia in methanol to obtain the target urea derivative.
| 【1】 Adhikari, S.S.; Hymavathi, L.; Sadalapure, K.; Sharma, G.V.M.; Sreenivas, P.; Mhaskar, S.V.; Lalitha, S.V.S.; Chorghade, M.S.; Murugaiah, A.M.S.; Prasad, T.R.; Reddy, B.S.; Gurjar, M.K.; Reddy, V.G.; Krishna, P.R. (LeukoSite, Inc.); Substd. oxygen alicyclic cpds., including methods for synthesis thereof. WO 0001381 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 32994 | (1R)-3-[(2R,3R)-3-(chloromethyl)oxiranyl]-1-[(4-fluorophenoxy)methyl]propyl benzenesulfonate | C19H20ClFO5S | 详情 | 详情 | |
| (XVII) | 32995 | [(2S,5S)-5-ethynyltetrahydro-2-furanyl]methyl 4-fluorophenyl ether; (2S,5S)-2-ethynyl-5-[(4-fluorophenoxy)methyl]tetrahydrofuran | C13H13FO2 | 详情 | 详情 | |
| (XVIII) | 10393 | Oxirane; Ethylene oxide | 75-21-8 | C2H4O | 详情 | 详情 |
| (XIX) | 19645 | 4-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-3-butyn-1-ol | C15H17FO3 | 详情 | 详情 | |
| (XX) | 19646 | 1-[([[(phenoxycarbonyl)oxy]amino]carbonyl)oxy]benzene | C14H11NO5 | 详情 | 详情 | |
| (XXI) | 19647 | (2S,5S)-2-[(4-fluorophenoxy)methyl]-5-(4-[(phenoxycarbonyl)[(phenoxycarbonyl)oxy]amino]-1-butynyl)tetrahydrofuran | C29H26FNO7 | 详情 | 详情 |