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【结 构 式】 
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【分子编号】34846 【品名】(2S)-2-[(benzyloxy)methoxy]propanal 【CA登记号】 |
【 分 子 式 】C11H14O3 【 分 子 量 】194.23036 【元素组成】C 68.02% H 7.27% O 24.71% |
合成路线1
该中间体在本合成路线中的序号：(XXVIII)Methyl (S)-lactate (XXVI) was protected as the benzyloxymethyl ether (XXVII) and subsequently reduced to aldehyde (XXVIII) with DIBAL in toluene at -78 C. Addition of ethylmagnesium bromide to this aldehyde (XXVIII) produced a diastereomeric mixture of carbinols. The required (2S,3R) isomer (XXIX) was isolated by column chromatography and then converted to brosylate ester (XXX) by reaction with 4-bromobenzenesulfonyl chloride. Nucleophilic displacement of the brosylate group of (XXX) by triazolone (XXV) produced the N-alkylated triazolone (XXXI). Then, acid cleavage of the benzyloxymethyl protec-ting group of (XXXI) provided alcohol (XXXII).
| 【1】 Saksena, A.K.; Girijavallabhan, V.M.; Lovey, R.G.; Pike, R.E.; Wang, H.; Liu, Y.-T.; Ganguly, A.K.; Bennett, F. (Schering Corp.); Tetrahydrofuran antifungals. EP 0773941; WO 9638443 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 18964 | 4-bromobenzenesulfonyl chloride | 98-58-8 | C6H4BrClO2S | 详情 | 详情 | |
| (XXV) | 16351 | 4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C32H32F2N8O3 | 详情 | 详情 | |
| (XXVI) | 17075 | propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate | 27871-49-4 | C4H8O3 | 详情 | 详情 |
| (XXVII) | 34845 | methyl (2S)-2-[(benzyloxy)methoxy]propanoate | C12H16O4 | 详情 | 详情 | |
| (XXVIII) | 34846 | (2S)-2-[(benzyloxy)methoxy]propanal | C11H14O3 | 详情 | 详情 | |
| (XXIX) | 34847 | (2S,3R)-2-[(benzyloxy)methoxy]-3-pentanol | C13H20O3 | 详情 | 详情 | |
| (XXX) | 34848 | (1R,2S)-2-[(benzyloxy)methoxy]-1-ethylpropyl 4-bromobenzenesulfonate | C19H23BrO5S | 详情 | 详情 | |
| (XXXI) | 34849 | 2-[(1S,2S)-2-[(benzyloxy)methoxy]-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C45H50F2N8O5 | 详情 | 详情 | |
| (XXXII) | 34850 | 4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one | C37H42F2N8O4 | 详情 | 详情 |