4-amino-1-[(2S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-5-fluoropyrimidin-2-one | 189818-67-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-amino-1-[(2S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-5-fluoropyrimidin-2-one
• CAS: 189818-67-5
• 化学式: C₂₅H₃₀FN₃O₃Si
• 分子量: 467.615
• InChiKey: BDRFFZITYOUGSN-GCJKJVERSA-N

物化性质

• 沸点：
  532.3±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(2S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-5-fluoropyrimidin-2-one 在 triethylamine trihydrofluoride 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到4-氨基-5-氟-1-[(2S,5R)-5-(羟基甲基)四氢呋喃-2-基]嘧啶-2-酮
  参考文献：
  名称：

  Stereoselective Syntheses of β-l-FD4C and β-l-FddC

  摘要：

  Stereocontrolled syntheses of two potent antiviral agents, beta-L-FD4C and beta-L-FddC, were accomplished both in 10-step sequences, with an overall yield of 27% and 25%, respectively. It is worthwhile to mention that the introduction of a phenylseleno moiety to the C-2 alpha position of the lactone 4 can now be performed in a stereocontrolled fashion, providing the key intermediate 5 alpha in 75% yield.

  DOI：

  10.1021/jo970177k
• 作为产物：
  描述：

  (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 、 苯 为溶剂， 反应 45.5h， 生成 4-amino-1-[(2S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-5-fluoropyrimidin-2-one
  参考文献：
  名称：

  Stereoselective Syntheses of β-l-FD4C and β-l-FddC

  摘要：

  Stereocontrolled syntheses of two potent antiviral agents, beta-L-FD4C and beta-L-FddC, were accomplished both in 10-step sequences, with an overall yield of 27% and 25%, respectively. It is worthwhile to mention that the introduction of a phenylseleno moiety to the C-2 alpha position of the lactone 4 can now be performed in a stereocontrolled fashion, providing the key intermediate 5 alpha in 75% yield.

  DOI：

  10.1021/jo970177k

文献信息

• Stereoselective Syntheses of β-<scp>l</scp>-FD4C and β-<scp>l</scp>-FddC
  作者：Shu-Hui Chen、Xiuyan Li、Jun Li、Chuansheng Niu、Ellen Carmichael、Terrence W. Doyle

  DOI：10.1021/jo970177k

  日期：1997.5.1

  Stereocontrolled syntheses of two potent antiviral agents, beta-L-FD4C and beta-L-FddC, were accomplished both in 10-step sequences, with an overall yield of 27% and 25%, respectively. It is worthwhile to mention that the introduction of a phenylseleno moiety to the C-2 alpha position of the lactone 4 can now be performed in a stereocontrolled fashion, providing the key intermediate 5 alpha in 75% yield.