5-[(E)-2-bromoethenyl]-1-[(2R,4S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl]-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】51554

【品名】5-[(E)-2-bromoethenyl]-1-[(2R,4S)-2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-1,3-dioxolan-4-yl]-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【分子式】C₁₆H₂₅BrN₂O₅Si

【分子量】433.37448

【元素组成】C 44.34% H 5.81% Br 18.44% N 6.46% O 18.46% Si 6.48%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

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)

参考文献中间体

合成目标

【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

Extended Information