dimethyl ((((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate | 1000863-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: dimethyl ((((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate
• CAS: 1000863-96-6
• 化学式: C₁₇H₂₀FN₂O₇PSe
• 分子量: 493.287
• InChiKey: UZIRPPKQZJAGMU-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl ((((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate 在 双氧水 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到1-[(2R,5R)-5-(dimethoxyphosphorylmethoxy)-2,5-dihydrofuran-2-yl]-5-fluoropyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038
• 作为产物：
  描述：

  苯基氯化硒 、 羟甲基膦酸二甲酯 、 1-(2,3-dihydro-furan-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione 在 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到dimethyl ((((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038