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【结 构 式】 
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【分子编号】32027 【品名】(1R,5R)-4-[(2S)-6-chloro-2-[(dibenzylene)amino]hexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione 【CA登记号】 |
【 分 子 式 】C29H35ClN2O3S 【 分 子 量 】527.12728 【元素组成】C 66.08% H 6.69% Cl 6.73% N 5.31% O 9.11% S 6.08% |
合成路线1
该中间体在本合成路线中的序号：(XV)The reaction of the labeled acylated (-)-bornane-10,2-sultam (XI) with benzophenone imine (XII) gives the glycylsultam derivative (XIII), which is alkylated with 4-iodobutyl chloride (XIV) by means of butyllithium and DMPU in THF yielding intermediate (XV). The selective hydrolysis of (XV) with HCl affords the omega-chloro-L-norleucine derivative (XVI), which is cyclized by means of tetrabutylammonium fluoride and DIEA in hot acetonitrile giving the (2S)-piperidyl derivative (XVII). Finally, this compound is hydrolyzed with LiOH in THF/water to the labeled intermediate (II).
| 【1】 Moenius, T.; et al.; C-14 labelling of NVP RAD001 - A new rapamycin derivative. J Label Compd Radiopharm 1999, 42, 1, 29. |
| 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) | 17380 | (2S)hexahydro-2-pyridinecarboxylic acid; (S)-pipecolic acid | 3105-95-1 | C6H11NO2 | 详情 | 详情 |
| (II) | 45303 | (2S)-2-piperidinecarboxylic acid | C6H11NO2 | 详情 | 详情 | |
| (XI) | 32030 | (1R,5R)-4-(2-bromoacetyl)-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C12H18BrNO3S | 详情 | 详情 | |
| (XI) | 45315 | (1R,5R)-4-(2-bromoacetyl)-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C12H18BrNO3S | 详情 | 详情 | |
| (XII) | 32024 | diphenylmethanimine | 1013-88-3 | C13H11N | 详情 | 详情 |
| (XIII) | 32025 | (1R,5R)-4-[2-[(dibenzylene)amino]acetyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C25H28N2O3S | 详情 | 详情 | |
| (XIII) | 45311 | (1R,5R)-4-[2-[(dibenzylene)amino]acetyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C25H28N2O3S | 详情 | 详情 | |
| (XIV) | 32026 | 1-chloro-4-iodobutane | 10297-05-9 | C4H8ClI | 详情 | 详情 |
| (XV) | 32027 | (1R,5R)-4-[(2S)-6-chloro-2-[(dibenzylene)amino]hexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C29H35ClN2O3S | 详情 | 详情 | |
| (XV) | 45312 | (1R,5R)-4-[(2S)-6-chloro-2-[(dibenzylene)amino]hexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C29H35ClN2O3S | 详情 | 详情 | |
| (XVI) | 32028 | (1R,5R)-4-[(2S)-2-amino-6-chlorohexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C16H27ClN2O3S | 详情 | 详情 | |
| (XVI) | 45313 | (1R,5R)-4-[(2S)-2-amino-6-chlorohexanoyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C16H27ClN2O3S | 详情 | 详情 | |
| (XVII) | 32029 | (1R,5R)-10,10-dimethyl-4-[(2S)piperidinylcarbonyl]-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C16H26N2O3S | 详情 | 详情 | |
| (XVII) | 45314 | (1R,5R)-10,10-dimethyl-4-[(2S)piperidinylcarbonyl]-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C16H26N2O3S | 详情 | 详情 |