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【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.

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 CAS号 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
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