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【结 构 式】 
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【分子编号】50462 【品名】1-(bromomethyl)-10-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)decyl acetate 【CA登记号】 |
【 分 子 式 】C20H31BrN4O4 【 分 子 量 】471.3947 【元素组成】C 50.96% H 6.63% Br 16.95% N 11.89% O 13.58% |
合成路线1
该中间体在本合成路线中的序号：(V)The alkylation of theobromine (I) with undecenyl mesylate (II) in the presence of NaH in DMSO afforded the 1-undecenyl xanthine (III). Dihydroxylation of the terminal double bond of (III) by means of N-methylmorpholine-N-oxide and a catalytic amount of potassium osmate gave diol (IV), which was further converted to bromo acetate (V) by treatment with a solution of HBr in AcOH. Methanolysis of the bromoester (V) with concomitant cyclization gave rise to epoxide (VI). Finally, epoxide opening upon heating with dodecylamine (VII) furnished the target amino alcohol.
| 【1】 Michnick, J.; Underiner, G.E.; Klein, J.P.; Rice, G.C.; Sunkara, P.S. (Cell Therapeutics, Inc.); Second messenger cell signaling inhibitors. CH 686830; EP 0719267; JP 1996508981; US 5470878; WO 9422863 . |
| 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) | 16651 | theobromine; 3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione | 83-67-0 | C7H8N4O2 | 详情 | 详情 |
| (II) | 50459 | 10-undecenyl methanesulfonate | C12H24O3S | 详情 | 详情 | |
| (III) | 50460 | 3,7-dimethyl-1-(10-undecenyl)-3,7-dihydro-1H-purine-2,6-dione | C18H28N4O2 | 详情 | 详情 | |
| (IV) | 50461 | 1-(10,11-dihydroxyundecyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione | C18H30N4O4 | 详情 | 详情 | |
| (V) | 50462 | 1-(bromomethyl)-10-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)decyl acetate | C20H31BrN4O4 | 详情 | 详情 | |
| (VI) | 50463 | 3,7-dimethyl-1-[9-(2-oxiranyl)nonyl]-3,7-dihydro-1H-purine-2,6-dione | C18H28N4O3 | 详情 | 详情 | |
| (VII) | 40735 | 1-dodecanamine; dodecylamine | 124-22-1 | C12H27N | 详情 | 详情 |