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【结 构 式】 
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【药物名称】 【化学名称】(6R,8R,9R)-N-Acetyl-N'-[4-amino-9-(tert-butyldimethylsilyloxy)-6-(tert-butyldimethylsilyloxymethyl)-1,7-dioxa-2-thiaspiro[4.4]-3-nonen-8-yl]urea S,S-dioxide 【CA登记号】 【 分 子 式 】C22H43N3O8SSi2 【 分 子 量 】565.83931 |
【开发单位】CSIC (Originator), Rega Institute for Medical Research (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Reverse Transcriptase Inhibitors |
合成路线1
The reduction of azide (I) with trimethylphosphine in THF gives the amine (II), which is treated with chlorosulfonyl isocyanate (A) in acetonitrile yielding the urea derivative (III). Finally, this compound is acetylated with acetic anhydride in pyridine to afford a mixture of alpha and beta acetylureas which is separated by centrifugal circular thin layer chromatography.
| 【1】 Velázquez, S.; Chamorro, C.; Perez-Perez, M.J.; Alvarez, R.; Jimeno, M.L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.J.; Abasic analogues of TSAO-T as the first sugar derivatives that specifically inhibit HIV-1 reverse transcriptase. J Med Chem 1998, 41, 23, 4636. |
| 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) | 14101 | Chlorosulfonyl isocyanate | 1189-71-5 | CClNO3S | 详情 | 详情 |
| (I) | 26923 | (6R,8R,9R)-4-amino-8-azido-9-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,7-dioxa-2lambda(6)-thiaspiro[4.4]non-3-ene-2,2-dione | C19H38N4O6SSi2 | 详情 | 详情 | |
| (II) | 26924 | (6R,8R,9R)-4,8-diamino-9-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,7-dioxa-2lambda(6)-thiaspiro[4.4]non-3-ene-2,2-dione | C19H40N2O6SSi2 | 详情 | 详情 | |
| (III) | 26926 | N-[(6R,8R,9R)-4-amino-9-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2,2-dioxo-1,7-dioxa-2lambda(6)-thiaspiro[4.4]non-3-en-8-yl]urea | C20H41N3O7SSi2 | 详情 | 详情 |