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【结 构 式】 
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【分子编号】26923 【品名】(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 【CA登记号】 |
【 分 子 式 】C19H38N4O6SSi2 【 分 子 量 】506.77108 【元素组成】C 45.03% H 7.56% N 11.06% O 18.94% S 6.33% Si 11.08% |
合成路线1
该中间体在本合成路线中的序号：(I)The reduction of azide (I) with trimethylphosphine in THF gives the amine (II), which is then treated with methacryloyl isocyanate (III) in acetonitrile yielding a mixture of alpha and beta phenylureas 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 |
|---|---|---|---|---|---|---|
| (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) | 26925 | 2-methylacryloyl isocyanate | C5H5NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)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 |
合成路线3
该中间体在本合成路线中的序号：(I)The reduction of azide (I) with trimethylphosphine in THF gives the amine (II), which is then treated with phenyl isocyanate (A) in acetonitrile yielding a mixture of alpha and beta phenylureas 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) | 11289 | 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate | 103-71-9 | C7H5NO | 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 |