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【结 构 式】 
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【分子编号】51553 【品名】(2R)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl acetate 【CA登记号】 |
【 分 子 式 】C12H24O5Si 【 分 子 量 】276.40506 【元素组成】C 52.15% H 8.75% O 28.94% Si 10.16% |
合成路线1
该中间体在本合成路线中的序号：(I)The condensation of the chiral dioxolane (I) with 5(E)-(2-bromovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II), which is purified by chromatography. Finally, this compound is deprotected by means of TBAF in acetonitrile. (1,2)
| 【1】 Gumina, G.; Li, L.; Lee, C.S.; Cheng, Y.-C.; Choi, Y.; Tsujii, E.; Grill, S.; Gullen, E.; Chu, C.K.; Structure-activity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses. J Med Chem 2000, 43, 13, 2538. |
| 【2】 Chu, C.K.; Cheng, Y.-C.; Li, L.; Chai, Y. (University of Georgia; Yale University); 5-(E)-Bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use. CA 2378370; EP 1204415; US 6653318; WO 0106986 . |
| 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) | 51553 | (2R)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl acetate | C12H24O5Si | 详情 | 详情 | |
| (II) | 38073 | 5-[(E)-2-bromoethenyl]-2,4(1H,3H)-pyrimidinedione | 69304-49-0 | C6H5BrN2O2 | 详情 | 详情 |
| (III) | 51554 | 5-[(E)-2-bromoethenyl]-1-[(2R,4S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl]-2,4(1H,3H)-pyrimidinedione | C16H25BrN2O5Si | 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 condensation of the chiral dioxolane (I) with 5(E)-(2-chlorovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II) that is purified by chromatography. Finally, this compound is deprotected by means of TBAF in acetonitrile.
| 【1】 Gumina, G.; Li, L.; Lee, C.S.; Cheng, Y.-C.; Choi, Y.; Tsujii, E.; Grill, S.; Gullen, E.; Chu, C.K.; Structure-activity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses. J Med Chem 2000, 43, 13, 2538. |
| 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) | 51553 | (2R)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl acetate | C12H24O5Si | 详情 | 详情 | |
| (II) | 51555 | 5-[(E)-2-chloroethenyl]-2,4(1H,3H)-pyrimidinedione | C6H5ClN2O2 | 详情 | 详情 | |
| (III) | 51556 | 1-[(2R,4S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl]-5-[(E)-2-chloroethenyl]-2,4(1H,3H)-pyrimidinedione | C16H25ClN2O5Si | 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 condensation of the chiral dioxolane (I) with 5(E)-(2-iodovinyl)uracil (II) by means of Tbdms-OTf and lutidine gives the silylated nucleoside (II), which is purified by chromatography. Finally, this compound is deprotected by means of TBAF in acetonitrile.
| 【1】 Gumina, G.; Li, L.; Lee, C.S.; Cheng, Y.-C.; Choi, Y.; Tsujii, E.; Grill, S.; Gullen, E.; Chu, C.K.; Structure-activity relationships of (E)-5-(2-bromovinyl)uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses. J Med Chem 2000, 43, 13, 2538. |
| 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) | 51553 | (2R)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl acetate | C12H24O5Si | 详情 | 详情 | |
| (II) | 51557 | 5-[(E)-2-iodoethenyl]-2,4(1H,3H)-pyrimidinedione | C6H5IN2O2 | 详情 | 详情 | |
| (III) | 51558 | 1-[(2R,4S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl]-5-[(E)-2-iodoethenyl]-2,4(1H,3H)-pyrimidinedione | C16H25IN2O5Si | 详情 | 详情 |