(1′α,2′R)-1′-(O4-methyluracil-1-yl)-2′-deoxy-2′-fluoro-3′-O-diisopropylphosphono-methyl-L-threose | 1446785-43-8

• 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: (1′α,2′R)-1′-(O4-methyluracil-1-yl)-2′-deoxy-2′-fluoro-3′-O-diisopropylphosphono-methyl-L-threose
• 英文别名: 1-[(2R,3R,4S)-4-[di(propan-2-yloxy)phosphorylmethoxy]-3-fluorooxolan-2-yl]-4-methoxypyrimidin-2-one
• CAS: 1446785-43-8
• 化学式: C₁₆H₂₆FN₂O₇P
• 分子量: 408.364
• InChiKey: PNOBYPYEUHIPRC-NWANDNLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1′α,2′R)-1′-(O4-methyluracil-1-yl)-2′-deoxy-2′-fluoro-3′-O-diisopropylphosphono-methyl-L-threose 在 三甲基溴硅烷 、 氨 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (1′α,2′R)-1′-(cytosin-1-yl)-2′-deoxy-2′-fluoro-3′-O-phosphonomethyl-L-threose
  参考文献：
  名称：

  Synthesis of α-l-Threose Nucleoside Phosphonates via Regioselective Sugar Protection

  摘要：

  A new synthesis route to a-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.

  DOI：

  10.1021/jo400907g
• 作为产物：
  描述：

  1-[(2R,4S)-4-[di(propan-2-yloxy)phosphorylmethoxy]-3-oxooxolan-2-yl]-4-methoxypyrimidin-2-one 在 sodium tetrahydroborate 、 二乙胺基三氟化硫 、 氟化氢吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (1′α,2′R)-1′-(O4-methyluracil-1-yl)-2′-deoxy-2′-fluoro-3′-O-diisopropylphosphono-methyl-L-threose
  参考文献：
  名称：

  Synthesis of α-l-Threose Nucleoside Phosphonates via Regioselective Sugar Protection

  摘要：

  A new synthesis route to a-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.

  DOI：

  10.1021/jo400907g

文献信息

• Synthesis of α-<scp>l</scp>-Threose Nucleoside Phosphonates via Regioselective Sugar Protection
  作者：Shrinivas G. Dumbre、Mi-Yeon Jang、Piet Herdewijn

  DOI：10.1021/jo400907g

  日期：2013.7.19

  A new synthesis route to a-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.