[(2R,3R,4S)-2-(6-benzamidopurin-7-yl)-4-[tert-butyl(diphenyl)silyl]oxyoxolan-3-yl] benzoate | 1446785-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,4S)-2-(6-benzamidopurin-7-yl)-4-[tert-butyl(diphenyl)silyl]oxyoxolan-3-yl] benzoate
• CAS: 1446785-51-8
• 化学式: C₃₉H₃₇N₅O₅Si
• 分子量: 683.839
• InChiKey: NIUBYNDTRDWITD-HICSEYKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S)-2-(6-benzamidopurin-7-yl)-4-[tert-butyl(diphenyl)silyl]oxyoxolan-3-yl] benzoate 在 四丁基氟化铵 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 1′α-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-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-O-acetyl-2-O-benzoyl-3-O-tert-butyldiphenylsilyl-L-threofuranose 、 N6-苯甲酰基腺嘌呤 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以51%的产率得到1′α-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-O-tert-butyldiphenylsilyl-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.