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【结 构 式】 
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【分子编号】45308 【品名】(1S,5S)-4-[(1R)-3-cyclohexen-1-ylcarbonyl]-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 】C17H25NO3S 【 分 子 量 】323.45644 【元素组成】C 63.13% H 7.79% N 4.33% O 14.84% S 9.91% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The reaction of the labeled acylated (+)-bornane-10,2-sultam (IV) with triethyl phosphite gives the phosphonate (V), which is treated with paraformaldehyde, galvinoxyl and K2CO3 yielding the acrylate derivative (VI). The cyclization of (VI) with butadiene (VII) by means of diethylaluminum chloride and galvinoxyl (as radical scavenger) affords the cyclohexene-carboxamide derivative (VIII), which is hydrolyzed with LiOH in THF/water giving the (1R)-3-cyclohexenecarboxylic acid (IX). The oxidation of (IX) with m-chloroperbenzoic acid and triethylamine in CCl4 yielded regioselectively the hydroxylactone (X), which is finally hydrolyzed with HCl to the labeled intermediate (I).
| 【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 |
|---|---|---|---|---|---|---|
| (I) | 32019 | (1R,3R,4R)-3,4-dihydroxycyclohexanecarboxylic acid | C7H12O4 | 详情 | 详情 | |
| (I) | 45302 | (1R,3R,4R)-3,4-dihydroxycyclohexanecarboxylic acid | C7H12O4 | 详情 | 详情 | |
| (IV) | 32020 | (1S,5S)-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 | |
| (IV) | 45305 | (1S,5S)-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 | |
| (V) | 32021 | diethyl 2-[(1S,5S)-10,10-dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]dec-4-yl]-2-oxoethylphosphonate | C16H28NO6PS | 详情 | 详情 | |
| (V) | 45306 | diethyl 2-[(1S,5S)-10,10-dimethyl-3,3-dioxo-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]dec-4-yl]-2-oxoethylphosphonate | C16H28NO6PS | 详情 | 详情 | |
| (VI) | 32022 | (1S,5S)-4-acryloyl-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C13H19NO3S | 详情 | 详情 | |
| (VI) | 45307 | (1S,5S)-4-acryloyl-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C13H19NO3S | 详情 | 详情 | |
| (VII) | 11579 | 1,3-Butadiene; Butadiene | 106-99-0 | C4H6 | 详情 | 详情 |
| (VIII) | 32023 | (1S,5S)-4-[(1R)-3-cyclohexen-1-ylcarbonyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C17H25NO3S | 详情 | 详情 | |
| (VIII) | 45308 | (1S,5S)-4-[(1R)-3-cyclohexen-1-ylcarbonyl]-10,10-dimethyl-3lambda(6)-thia-4-azatricyclo[5.2.1.0(1,5)]decane-3,3-dione | C17H25NO3S | 详情 | 详情 | |
| (IX) | 11581 | (1R)-3-Cyclohexene-1-carboxylic acid | C7H10O2 | 详情 | 详情 | |
| (IX) | 45309 | (1R)-3-cyclohexene-1-carboxylic acid | C7H10O2 | 详情 | 详情 | |
| (X) | 11528 | (1R,4R,5R)-4-Hydroxy-6-oxabicyclo[3.2.1]octan-7-one | C7H10O3 | 详情 | 详情 | |
| (X) | 45310 | (1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one | C7H10O3 | 详情 | 详情 |