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【结 构 式】 
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【分子编号】25359 【品名】(1R)-1-[3-[2-(tert-butoxy)-2-oxoethoxy]phenyl]-3-(3,4-dimethoxyphenyl)propyl (2S)-2-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C29H39NO7 【 分 子 量 】513.6312 【元素组成】C 67.82% H 7.65% N 2.73% O 21.8% |
合成路线1
该中间体在本合成路线中的序号：(XX)In an alternative procedure, the intermediate alcohol (VIII) was coupled with N-Fmoc-(S)-pipecolic acid (XVIII) using DCC and DMAP to give ester (XIX). Subsequent deprotection of the Fmoc group of (XIX) by means of pyrrolidine provided amine (XX). This was further coupled to racemic 2-(3,4,5-trimethoxyphenyl)butyric acid (X), and the resulting diastereomeric mixture of amides (XXI) was separated by column chromatography. Then, TFA-promoted cleavage of the tert-butyl ester from the desired (S,S)-diastereoisomer provided carboxylic acid (XXII), which was finally coupled to ethylenediamine in the same way as before.
| 【1】 Clackson, T.; Yang, W.; Rozamus, L.W.; Hatada, M.; Amara, J.F.; Rollins, C.T.; Stevenson, L.F.; Magari, S.R.; Wood, S.A.; Courage, N.L.; Lu, X.; Cerasoli, F. Jr; Gilman, M.; Holt, D.A.; Redesigning an FKBP-ligand interface to generate chemical dimerizers with novel specificity. Proc Natl Acad Sci USA 1998, 95, 18, 10437. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 25348 | tert-butyl 2-[3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy]acetate | C23H30O6 | 详情 | 详情 | |
| (X) | 25350 | 2-(3,4,5-trimethoxyphenyl)butyric acid | C13H18O5 | 详情 | 详情 | |
| (XVIII) | 25357 | (2S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-piperidinecarboxylic acid | C21H21NO4 | 详情 | 详情 | |
| (XIX) | 25358 | 2-[(1R)-1-[3-[2-(tert-butoxy)-2-oxoethoxy]phenyl]-3-(3,4-dimethoxyphenyl)propyl] 1-(9H-fluoren-9-ylmethyl) (2S)-1,2-piperidinedicarboxylate | C44H49NO9 | 详情 | 详情 | |
| (XX) | 25359 | (1R)-1-[3-[2-(tert-butoxy)-2-oxoethoxy]phenyl]-3-(3,4-dimethoxyphenyl)propyl (2S)-2-piperidinecarboxylate | C29H39NO7 | 详情 | 详情 | |
| (XXI) | 25360 | (1R)-1-[3-[2-(tert-butoxy)-2-oxoethoxy]phenyl]-3-(3,4-dimethoxyphenyl)propyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)butanoyl]-2-piperidinecarboxylate | C42H55NO11 | 详情 | 详情 | |
| (XXII) | 25361 | 2-(3-[(1R)-3-(3,4-dimethoxyphenyl)-1-[([(2S)-1-[(2S)-2-(3,4,5-trimethoxyphenyl)butanoyl]piperidinyl]carbonyl)oxy]propyl]phenoxy)acetic acid | C38H47NO11 | 详情 | 详情 |