(1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose | 1446785-65-4

• 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: (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose
• 英文别名: [(2R,3R,4S)-2-(6-benzamidopurin-9-yl)-4-[di(propan-2-yloxy)phosphorylmethoxy]-4-ethynyloxolan-3-yl] benzoate
• CAS: 1446785-65-4
• 化学式: C₃₂H₃₄N₅O₈P
• 分子量: 647.624
• InChiKey: GJRDPJWQMTUCHE-LEFKNYOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-L-threose 在 三正丁胺 、 氨 、 三甲基硅咪唑 、 六甲基二硅氮烷 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 (1′α,3′S)-1′-(adenin-9-yl)-3′-ethynyl-3′-O-(diphosphatephosphonomethyl)-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：

  N6-苯甲酰基腺嘌呤 在 N,O-双三甲硅基乙酰胺 、 cerium(III) chloride 、 四丁基氟化铵 、 水 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 mineral oil 为溶剂， 反应 9.33h， 生成 (1′α,3′S)-1′-(N6-benzoyladenin-9-yl)-2′-O-benzoyl-3′-ethynyl-3′-O-(diisopropylphosphonomethyl)-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.