[(2S,4S)-4-[5-[(E)-2-bromoethenyl]-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl]methyl acetate -Drug Synthesis Database

【结构式】

【分子编号】39267

【品名】[(2S,4S)-4-[5-[(E)-2-bromoethenyl]-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl]methyl acetate

【CA登记号】

【分子式】C₁₂H₁₃BrN₂O₆

【分子量】361.1491

【元素组成】C 39.91% H 3.63% Br 22.12% N 7.76% O 26.58%

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：(V)

Hydrogenolysis of benzyl ether (I) in the presence of Pd/C afforded dioxolane alcohol (II), which was acetylated with Ac2O and pyridine to give diacetate (III). Subsequent condensation of (III) with the silylated (2-bromovinyl)uracil (IV) led to a diastereomeric mixture of nucleosides (V) and (VI). After chromatographic isolation of the desired isomer (V), hydrolysis of the acetate ester using K2CO3 in MeOH yielded the title compound.

参考文献中间体

合成目标

【1】 Dixit, D.M.; Wang, W.; Yuen, L.; Jin, H.; Bednarski, K.; Evans, C.A.; Mansour, T.S.; Inhibitory activities of herpes simplex viruses type 1 and 2 and human cytomegalovirus by stereoisomers of 2'-deoxy-3'-oxa-5(E)-(bromovinyl)uridines and their 4'-thio analogues. Bioorg Med Chem Lett 1994, 4, 22, 2667.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	39263	(2S)-2-[(benzyloxy)methyl]-1,3-dioxolan-4-yl acetate	C₁₃H₁₆O₅	详情	详情
(II)	39264	(2S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl acetate	C₆H₁₀O₅	详情	详情
(III)	39265	[(2S)-4-(acetoxy)-1,3-dioxolan-2-yl]methyl acetate	C₈H₁₂O₆	详情	详情
(IV)	39266	5-[(E)-2-bromoethenyl]-2,4-bis[(trimethylsilyl)oxy]pyrimidine; 5-[(E)-2-bromoethenyl]-2-[(trimethylsilyl)oxy]-4-pyrimidinyl trimethylsilyl ether	C₁₂H₂₁BrN₂O₂Si₂	详情	详情
(V)	39267	[(2S,4S)-4-[5-[(E)-2-bromoethenyl]-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl]methyl acetate	C₁₂H₁₃BrN₂O₆	详情	详情
(VI)	39268	[(2S,4R)-4-[5-[(E)-2-bromoethenyl]-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-1,3-dioxolan-2-yl]methyl acetate	C₁₂H₁₃BrN₂O₆	详情	详情

Extended Information