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【结 构 式】 
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【药物名称】 【化学名称】1,5-Dideoxy-1,5-[3-(trimethylsilyl)-2(E)-propen-1-ylimino]-D-glucitol 【CA登记号】 【 分 子 式 】C12H25NO4Si 【 分 子 量 】275.42335 |
【开发单位】Aventis Pharma (Originator) 【药理作用】AIDS Medicines, Antidiabetic Drugs, Anti-HIV Agents, ANTIINFECTIVE THERAPY, ENDOCRINE DRUGS, alpha-Glucosidase Inhibitors, Iminosugars |
合成路线1
Treatment of propargyl alcohol (I) with two equivalents of butyllithium in THF, followed by chlorotrimethylsilane, and then with methanol and a catalytic amount of distannoxane, gave 3-(trimethylsilyl)-2-propyn-1-ol (II). Partial reduction of acetylenic triple bond with sodium bis(2-methoxyethoxy)aluminum hydride afforded the expected (E)-olefin (III), which on treatment with methanesulfonyl chloride and triethylamine in dichloromethane provided mesylate (IV). Finally, alkylation of 1-deoxynojirimycin (V) with mesylate (IV) in the presence of triethylamine gave the title compound.
| 【1】 Lesur, B.; et al.; New deoxynojirimycin derivatives as potent inhibitors of intestinal alpha-glucohydrolases. Bioorg Med Chem Lett 1997, 7, 3, 355-360. |
| 【2】 Lesur, B.; Ducep, J.-B.; Danzin, C. (Merrell Pharmaceuticals, Inc.); Novel nojirimycin derivs.. EP 0453692; EP 0454580; JP 1993086072; US 5252587; US 5536732 . |
| 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) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
| (II) | 17941 | 3-Trimethylsilylpropargyl alcohol; 3-(trimethylsilyl)-2-propyn-1-ol | 5272-36-6 | C6H12OSi | 详情 | 详情 |
| (III) | 17942 | (E)-3-(trimethylsilyl)-2-propen-1-ol; trans-3-(Trimethylsilyl)allyl alcohol | 59376-64-6 | C6H14OSi | 详情 | 详情 |
| (IV) | 17943 | (E)-3-(trimethylsilyl)-2-propenyl methanesulfonate | C7H16O3SSi | 详情 | 详情 | |
| (V) | 17944 | deoxynojirimycin; (2R,3R,4R,5S)-2-(hydroxymethyl)-3,4,5-piperidinetriol | 19130-96-2 | C6H13NO4 | 详情 | 详情 |