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【结 构 式】 
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【分子编号】62153 【品名】(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 【CA登记号】 |
【 分 子 式 】C19H29NO3S 【 分 子 量 】351.5102 【元素组成】C 64.92% H 8.32% N 3.98% O 13.65% S 9.12% |
合成路线1
该中间体在本合成路线中的序号：(XVI)Wittig reaction of aldehyde (X) with phosphorane (II) produces the unsaturated ester (XI), which is further reduced to the allylic alcohol (XII) with DIBAL in toluene. Treatment of (XII) with CBr4 and PPh3 leads to allyl bromide (XIII). This is then condensed with sodium p-toluenesulfinate (XIV), providing sulfone (XV). Subsequent acidic Boc group cleavage gives amine (XVI).
| 【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 |
|---|---|---|---|---|---|---|
| (II) | 37071 | ethyl 2-(triphenylphosphoranylidene)propanoate | 5717-37-3 | C23H23O2P | 详情 | 详情 |
| (X) | 62147 | tert-butyl (2R,3R,5S,6S)-2,5-dimethyl-6-(2-oxoethyl)tetrahydro-2H-pyran-3-ylcarbamate | C14H25NO4 | 详情 | 详情 | |
| (XI) | 62148 | ethyl (E)-4-{(2S,3S,5R,6R)-5-[(tert-butoxycarbonyl)amino]-3,6-dimethyltetrahydro-2H-pyran-2-yl}-2-methyl-2-butenoate | C19H33NO5 | 详情 | 详情 | |
| (XII) | 62149 | tert-butyl (2R,3R,5S,6S)-6-[(E)-4-hydroxy-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate | C17H31NO4 | 详情 | 详情 | |
| (XIII) | 62150 | tert-butyl (2R,3R,5S,6S)-6-[(E)-4-bromo-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate | C17H30BrNO3 | 详情 | 详情 | |
| (XIV) | 62151 | 4-methylbenzenesulfinate | C7H7O2S | 详情 | 详情 | |
| (XV) | 62152 | tert-butyl (2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-ylcarbamate | C24H37NO5S | 详情 | 详情 | |
| (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 |
合成路线2
该中间体在本合成路线中的序号：(XVI)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 |