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【结 构 式】 
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【药物名称】3-Deazauridine, NSC-126849, DAU 【化学名称】4-Hydroxy-1-(beta-D-ribofuranosyl)-2-pyridone 【CA登记号】23205-42-7 【 分 子 式 】C10H13NO6 【 分 子 量 】243.21821 |
【开发单位】Sigma Chemical (Originator), Valeant (Originator) 【药理作用】ONCOLYTIC DRUGS |
合成路线1
Treatment of 2,4-dihydroxypyridine (I) with hexamethyldisilazane (A) gives 2,4-bis(trimethylsilyloxy)pyridine (II). Condensation of (II) with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (III) gives a 68% yield 2',3',5'-tri-O-benzoyl-3-deazauridine (IV). Deblocking of (IV) with alcoholic ammonia gives 3-deazauridine in 88% crude yield.
| 【1】 Currie, B.L.; et al.; Synthesis of 3-deazauridine-[4-hydoxy-1-(beta-D-ribofuranosyl)-2-pyridone]. Chem Commun 1968, 1547-48. |
| 【2】 Currie, B.L.; et al.; The synthesis of 3-deazapyrimidine nucleosides related to uridine and cytidine and their derivatives. J Heterocycl Chem 1970, 7, 323-329. |
| 【3】 Chang, P.; 3-Deazauridine. Drugs Fut 1984, 9, 10, 739. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 34273 | N,N-bis(trimethylsilyl)amine; trimethyl-N-(trimethylsilyl)silanamine | 999-97-3 | C6H19NSi2 | 详情 | 详情 |
| (I) | 34269 | 2,4-pyridinediol | 626-03-9 | C5H5NO2 | 详情 | 详情 |
| (II) | 34270 | trimethylsilyl 2-[(trimethylsilyl)oxy]-4-pyridinyl ether; 2,4-bis[(trimethylsilyl)oxy]pyridine | C11H21NO2Si2 | 详情 | 详情 | |
| (III) | 34271 | benzyl (2R,3S,4R)-4-(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydro-3-furanyl ether; (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-bromotetrahydrofuran | C26H27BrO4 | 详情 | 详情 | |
| (IV) | 34272 | 1-[(2R,3R,4S,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]tetrahydro-2-furanyl]-4-hydroxy-2(1H)-pyridinone | C31H31NO6 | 详情 | 详情 |
Extended Information