4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】37573

【品名】4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone

【CA登记号】

【分子式】C₉H₁₂FN₃O₄

【分子量】245.2105032

【元素组成】C 44.08% H 4.93% F 7.75% N 17.14% O 26.1%

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：(IV)

The reaction of 3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide (I) with tris(trimethylsilyl)cytosine (II) in methylene chloride gives 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (III), which is hydrolyzed by treatment with methanol NH3 to afford 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)cytosine (IV). Finally, this compound is iodinated by treatment with HIO3 - I2 in CCl4 - H2O - acetic acid.

参考文献中间体

合成目标

【1】 Lopez, C.; Reichman, U.; Fox, J.; Hirota, K.; Watanabe, K.A.; Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem 1979, 22, 1, 21-24.
【2】 Thorpe, P.J.; Castaner, J.; FIAC. Drugs Fut 1981, 6, 7, 410.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29116	[(2R,3R,4S,5S)-3-(acetoxy)-5-bromo-4-fluorotetrahydro-2-furanyl]methyl benzoate	C₁₄H₁₄BrFO₅	详情	详情
(II)	37571	4-[bis(trimethylsilyl)amino]-1-(trimethylsilyl)-2(1H)-pyrimidinone	C₁₃H₂₉N₃OSi₃	详情	详情
(III)	37572	[(2R,3R,4S,5R)-3-(acetoxy)-5-[4-amino-2-oxo-1(2H)-pyrimidinyl]-4-fluorotetrahydro-2-furanyl]methyl benzoate	C₁₈H₁₈FN₃O₆	详情	详情
(IV)	37573	4-amino-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone	C₉H₁₂FN₃O₄	详情	详情

Extended Information