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【结 构 式】 
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【分子编号】62158 【品名】(Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-N-((2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-yl)-2-pentenamide 【CA登记号】 |
【 分 子 式 】C40H53NO5SSi 【 分 子 量 】688.01606 【元素组成】C 69.83% H 7.76% N 2.04% O 11.63% S 4.66% Si 4.08% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Horner-Emmons condensation of aldehyde (XVII) with phosphonate (XVIII) gives rise to the Z-olefin (XIX). After ester group hydrolysis, the resultant carboxylic acid (XX) is coupled to amine (XVI) by using HBTU to produce amide (XXI).
| 【1】 Horigome, M.; Motoyoshi, H.; Watanabe, H.; Kitahara, T.; A synthesis of FR901464. Tetrahedron Lett 2001, 42, 46, 8207. |
| 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) | 62153 | (2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-amine; (2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-ylamine | C19H29NO3S | 详情 | 详情 | |
| (XVII) | 62154 | (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}propanal | C19H24O2Si | 详情 | 详情 | |
| (XVIII) | 62155 | ethyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate | C8H11F6O5P | 详情 | 详情 | |
| (XIX) | 62156 | ethyl (Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate | C23H30O3Si | 详情 | 详情 | |
| (XX) | 62157 | (Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoic acid | C21H26O3Si | 详情 | 详情 | |
| (XXI) | 62158 | (Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-N-((2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-yl)-2-pentenamide | C40H53NO5SSi | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXI)Condensation of sulfone (XXI) with aldehyde (XXXVII), followed by treatment with benzoyl chloride affords adduct (XXXVIII). Reductive elimination of sulfone (XXXVIIII) with sodium amalgam leads to the conjugated diene (XXXIX). Both O-silyl groups of (XXXIX) are removed by treatment with tetrabutylammonium fluoride, providing diol (XL). Then, esterification of (XL) with acetic anhydride and DMAP furnishes diacetate (XLI).
| 【1】 Horigome, M.; Motoyoshi, H.; Watanabe, H.; Kitahara, T.; A synthesis of FR901464. Tetrahedron Lett 2001, 42, 46, 8207. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXI) | 62158 | (Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-N-((2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-yl)-2-pentenamide | C40H53NO5SSi | 详情 | 详情 | |
| (XXVII) | 62173 | (2S,3S,6S)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-carbaldehyde | C15H28O4Si | 详情 | 详情 | |
| (XXXVIII) | 62174 | (1S,3E)-1-((2R,3S,6S)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl)-5-{(2S,3S,5R,6R)-5-[((Z,4S)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoyl)amino]-3,6-dimethyltetrahydro-2H-pyran-2-yl}-3-methyl-2-[(4-methylphenyl)sulfonyl]-3-pentenyl benzoate | C62H85NO10SSi2 | 详情 | 详情 | |
| (XXXIX) | 62175 | (Z,4S)-N-{(2R,3R,5S,6S)-6-[(2E,4E)-5-((2R,3S,6S)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl)-3-methyl-2,4-pentadienyl]-2,5-dimethyltetrahydro-2H-pyran-3-yl}-4-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenam | C48H73NO6Si2 | 详情 | 详情 | |
| (XL) | 62176 | (Z,4S)-4-hydroxy-N-((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-hydroxy-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)-2-pentenamide | C26H41NO6 | 详情 | 详情 | |
| (XLI) | 62177 | (1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-(acetyloxy)-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate | C30H45NO8 | 详情 | 详情 |