5'-O-(p-monomethoxytrityl)-2'-O,3'-C-((3-methylidene)ethylene)-3'-deoxy-3'-dehydro-3'-C-(S)-hydroxymethyl-ribothymidine | 156271-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(p-monomethoxytrityl)-2'-O,3'-C-((3-methylidene)ethylene)-3'-deoxy-3'-dehydro-3'-C-(S)-hydroxymethyl-ribothymidine
• CAS: 156271-05-5
• 化学式: C₃₄H₃₄N₂O₇
• 分子量: 582.653
• InChiKey: PCSGKCNLYLIYRB-RCANGYALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112.01
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-(p-monomethoxytrityl)-2'-O,3'-C-((3-methylidene)ethylene)-3'-deoxy-3'-dehydro-3'-C-(S)-hydroxymethyl-ribothymidine 在 溶剂黄146 作用下， 以87%的产率得到2'-O,3'-C-((3-methylidene)ethylene)-3'-deoxy-3'-dehydro-3'-C-(S)-hydroxymethyl-ribothymidine
  参考文献：
  名称：

  The synthesis of new 3′-bis--substituted-3′-deoxy-3′-dehydro-[3.3.0]-α-fused thymidines by intramolecular radical trapping by tethered acetylenes

  摘要：

  The Michael addition reaction of propargyl alcohol with 3'-nitro-olefin I and subsequent Henry reaction at C-3' with electron deficient reagents has produced various diastereomeric mixtures of 2'-Q-propynyl-3'-deoxy-3- dehydro-3'-C-substituted-3'-nitro-thymidine derivatives 4 - 7 [alpha-substitution (major); beta-substitution (minor)] in 55-80% yield. Subsequently, the intramolecular cyclization-trapping of carbon radicals by tethered acetylene in 4 - 7 by the treatment with Bu(3)SnH and AIBN afforded 3'-bis-C-substituted-[3.3.0]-cis-fused thymidines 8 - 11 in 86-90% yield. The results detailed here represent the first examples of title compounds using a three-step procedure: (1) Michael addition of the propargyl alcohol to nitro-olefin, (2) Henry reaction with electron-deficient reagents, and (3) subsequent inramolecular cyclization-trapping of tertiary carbon radicals by a tethered acetylene.

  DOI：

  10.1016/s0040-4020(01)90436-3
• 作为产物：
  描述：

  1-<5-O-(p-monomethoxytrityl)-2-O-(R)-(2-propynyl)-3-deoxy-3-dehydro-3-C-(R)-hydroxymethyl-3-nitro-β-D-pentofuranosyl>thymine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以88%的产率得到5'-O-(p-monomethoxytrityl)-2'-O,3'-C-((3-methylidene)ethylene)-3'-deoxy-3'-dehydro-3'-C-(S)-hydroxymethyl-ribothymidine
  参考文献：
  名称：

  The synthesis of new 3′-bis--substituted-3′-deoxy-3′-dehydro-[3.3.0]-α-fused thymidines by intramolecular radical trapping by tethered acetylenes

  摘要：

  The Michael addition reaction of propargyl alcohol with 3'-nitro-olefin I and subsequent Henry reaction at C-3' with electron deficient reagents has produced various diastereomeric mixtures of 2'-Q-propynyl-3'-deoxy-3- dehydro-3'-C-substituted-3'-nitro-thymidine derivatives 4 - 7 [alpha-substitution (major); beta-substitution (minor)] in 55-80% yield. Subsequently, the intramolecular cyclization-trapping of carbon radicals by tethered acetylene in 4 - 7 by the treatment with Bu(3)SnH and AIBN afforded 3'-bis-C-substituted-[3.3.0]-cis-fused thymidines 8 - 11 in 86-90% yield. The results detailed here represent the first examples of title compounds using a three-step procedure: (1) Michael addition of the propargyl alcohol to nitro-olefin, (2) Henry reaction with electron-deficient reagents, and (3) subsequent inramolecular cyclization-trapping of tertiary carbon radicals by a tethered acetylene.

  DOI：

  10.1016/s0040-4020(01)90436-3