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【结 构 式】 
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【分子编号】41035 【品名】(2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate 【CA登记号】 |
【 分 子 式 】C12H16N2O9S2 【 分 子 量 】396.39912 【元素组成】C 36.36% H 4.07% N 7.07% O 36.33% S 16.18% |
合成路线1
该中间体在本合成路线中的序号：(II)An improved process for the preparation of high purity stavudine in a good yield was reported: The reaction of 5-methyluridine (I) with mesyl chloride and NMM in acetone, followed by a treatment with 6N NaOH gives the 2,2'-anhydro-5-methyluridine derivative (II), which is treated successively with potassium benzoate in DMF, HBr in acetic acid, and finally with Zn in DMF to yield 2',3'-anhydro-5'-O-benzoylthymidine (III). Finally, this compound is debenzoylated with hot butylamine.
| 【1】 Reddy, J.P.; Quinlan, S.L.; Reid, J.G.; Renner, D.A.; Weaver, D.G.; Stark, D.R.; Chen, B.-C.; Independent syntesis and fate studies of impurities in process intermediates of the anti-AIDS drug d4T. Org Process Res Dev 1998, 2, 3, 203. |
| 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) | 12206 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione; 5-Methyluridine | 1463-10-1 | C10H14N2O6 | 详情 | 详情 |
| (II) | 41035 | (2R,3R,3aS,9aR)-7-methyl-2-[[(methylsulfonyl)oxy]methyl]-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-yl methanesulfonate | C12H16N2O9S2 | 详情 | 详情 | |
| (III) | 12254 | [(2S,5R)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl benzoate | C17H16N2O5 | 详情 | 详情 |