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【结 构 式】 
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【分子编号】40558 【品名】tert-butyl (1R)-1-(3-[3-[(1S)-1-amino-2-hydroxyethyl]-5-methoxyphenoxy]-4-methoxyphenyl)-2-(benzyloxy)ethylcarbamate 【CA登记号】 |
【 分 子 式 】C30H38N2O7 【 分 子 量 】538.641 【元素组成】C 66.9% H 7.11% N 5.2% O 20.79% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The dipeptide intermediate (XI) has been obtained as follows: The coupling of the two synthons (I) and (II) by means of K2CO3 and 18-C-6 in DMSO gives the diphenyl ether (III), which is reduced at its nitro group with H2 over Pd/C yielding the amine (IV). The treatment of (IV) with tert-butyl nitrite, HBF4 and Cu2O affords the phenol (V), which is methylated with MeI and K2CO3 to provide the corresponding methyl ether (VI). The protection of the primary alcohol of (VI) with benzyl bromide (A) and K2CO3 gives the benzyl ether (VII), which is deprotected at the Mem and trifluoroacetamido groups yielding the aminoethanol derivative (VIII). The condensation of (VIII) with the protected phenylalanine derivative (IX) by means of EDC and HOBT affords the corresponding amide (X), which is finally oxidized with Dess Martin periodinane (DMP) and NaClO2 to afford the desired dipeptide intermediate (XI).
| 【1】 Boger, D.L.; et al.; First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc 2001, 123, 9, 1862. |
| 【2】 Boger, D.L.; et al.; Total synthesis of the teicoplanin aglycon. J Am Chem Soc 2000, 122, 30, 7416. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (I) | 40551 | 2,2,2-trifluoro-N-[(1S)-1-(3-hydroxy-5-methoxyphenyl)-2-[(2-methoxyethoxy)methoxy]ethyl]acetamide | C15H20F3NO6 | 详情 | 详情 | |
| (II) | 40552 | tert-butyl (1R)-1-(3-fluoro-4-nitrophenyl)-2-hydroxyethylcarbamate | C13H17FN2O5 | 详情 | 详情 | |
| (III) | 40553 | tert-butyl (1R)-2-hydroxy-1-[3-(3-methoxy-5-[(1S)-2-[(2-methoxyethoxy)methoxy]-1-[(2,2,2-trifluoroacetyl)amino]ethyl]phenoxy)-4-nitrophenyl]ethylcarbamate | C28H36F3N3O11 | 详情 | 详情 | |
| (IV) | 40554 | tert-butyl (1R)-1-[4-amino-3-(3-methoxy-5-[(1S)-2-[(2-methoxyethoxy)methoxy]-1-[(2,2,2-trifluoroacetyl)amino]ethyl]phenoxy)phenyl]-2-hydroxyethylcarbamate | C28H38F3N3O9 | 详情 | 详情 | |
| (V) | 40555 | tert-butyl (1R)-2-hydroxy-1-[4-hydroxy-3-(3-methoxy-5-[(1S)-2-[(2-methoxyethoxy)methoxy]-1-[(2,2,2-trifluoroacetyl)amino]ethyl]phenoxy)phenyl]ethylcarbamate | C28H37F3N2O10 | 详情 | 详情 | |
| (VI) | 40556 | tert-butyl (1R)-2-hydroxy-1-[4-methoxy-3-(3-methoxy-5-[(1S)-2-[(2-methoxyethoxy)methoxy]-1-[(2,2,2-trifluoroacetyl)amino]ethyl]phenoxy)phenyl]ethylcarbamate | C29H39F3N2O10 | 详情 | 详情 | |
| (VII) | 40557 | tert-butyl (1R)-2-(benzyloxy)-1-[4-methoxy-3-(3-methoxy-5-[(1S)-2-[(2-methoxyethoxy)methoxy]-1-[(2,2,2-trifluoroacetyl)amino]ethyl]phenoxy)phenyl]ethylcarbamate | C36H45F3N2O10 | 详情 | 详情 | |
| (VIII) | 40558 | tert-butyl (1R)-1-(3-[3-[(1S)-1-amino-2-hydroxyethyl]-5-methoxyphenoxy]-4-methoxyphenyl)-2-(benzyloxy)ethylcarbamate | C30H38N2O7 | 详情 | 详情 | |
| (IX) | 40559 | (2R)-3-(4-fluoro-3-nitrophenyl)-2-(propionylamino)propionic acid | C12H13FN2O5 | 详情 | 详情 | |
| (X) | 40560 | tert-butyl (1R)-2-(benzyloxy)-1-[3-[3-((1S)-1-[[(2R)-3-(4-fluoro-3-nitrophenyl)-2-(propionylamino)propanoyl]amino]-2-hydroxyethyl)-5-methoxyphenoxy]-4-methoxyphenyl]ethylcarbamate | C42H49FN4O11 | 详情 | 详情 | |
| (XI) | 40561 | (2S)-2-[3-(5-[(1R)-2-(benzyloxy)-1-[(tert-butoxycarbonyl)amino]ethyl]-2-methoxyphenoxy)-5-methoxyphenyl]-2-[[(2R)-3-(4-fluoro-3-nitrophenyl)-2-(propionylamino)propanoyl]amino]ethanoic acid | C42H47FN4O12 | 详情 | 详情 |