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【结 构 式】 
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【分子编号】63837 【品名】8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione 【CA登记号】 |
【 分 子 式 】C20H28N4O3 【 分 子 量 】372.46748 【元素组成】C 64.49% H 7.58% N 15.04% O 12.89% |
合成路线1
该中间体在本合成路线中的序号：M1The oxidation of tricyclo[3.3.1.03,7]nonane-3-carboxylic acid methyl ester (I) with CrO3 in acetic anhydride/acetic acid gives a mixture of the 9-oxo and 6-oxo isomers (II), which is condensed with 5,6-diamino-1,3-dipropylpyrimidine-2,4(1H,3H)-dione (III) by means of LiOH, and after HPLC separation yields the 9-oxo isomer (IV) of the condensation product. The cyclization of (IV) by means of Ca(OH)2 affords the 1,3-dipropylxanthine derivative (V), which is finally reduced with LiBH4 to a mixture of isomers that is separated by HPLC yielding finally metabolite M1.
| 【1】 Shimada, J.; Eguchi, T.; Yasuzawa, T.; Nakamura, A.; Horiguchi, A.; Mochida, K.; Suzuki, F.; Synthesis of rat metabolites of a adenosine A1 antagonist, KW-3902. Symp Med Chem 1996, Abst 1-P-24. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIa) | 20541 | methyl 9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxylate | C11H14O3 | 详情 | 详情 | |
| (IIb) | 20542 | methyl 6-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxylate | C11H14O3 | 详情 | 详情 | |
| M1 | 63837 | 8-(9-hydroxytricyclo[3.3.1.0~3,7~]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione | C20H28N4O3 | 详情 | 详情 | |
| (I) | 20540 | methyl tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate | C11H16O2 | 详情 | 详情 | |
| (III) | 14628 | 5,6-diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione | C10H18N4O2 | 详情 | 详情 | |
| (IV) | 20544 | N-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-5-pyrimidinyl)-9-oxotricyclo[3.3.1.0(3,7)]nonane-3-carboxamide | C20H28N4O4 | 详情 | 详情 | |
| (V) | 20545 | 8-(9-oxotricyclo[3.3.1.0(3,7)]non-3-yl)-1,3-dipropyl-3,7-dihydro-1H-purine-2,6-dione | C20H26N4O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：M1The selective biological hydroxylation of compounds (XII) by means of Absidia ramosa FERM BP-4605 in corn steep liquor, glucose, Brig 35 at 28 C, 5-7 days gives metabolites M1.
| 【1】 Shimada, J.; Eguchi, T.; Yasuzawa, T.; Nakamura, A.; Horiguchi, A.; Mochida, K.; Suzuki, F.; Synthesis of rat metabolites of a adenosine A1 antagonist, KW-3902. Symp Med Chem 1996, Abst 1-P-24. |