3'-C,4'-C-(3-oxa-4-azapentylene)thymidine | 1161846-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: 3'-C,4'-C-(3-oxa-4-azapentylene)thymidine
• 英文别名: 1-[(2R,3aS,8aR)-3a-hydroxy-8a-(hydroxymethyl)-2,3,4,5,7,8-hexahydrofuro[2,3-d]oxazepin-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1161846-22-5
• 化学式: C₁₃H₁₉N₃O₆
• 分子量: 313.31
• InChiKey: FKVDMFICTLMBTI-JIMOISOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3'-C,4'-C-(N-benzyloxycarbonyl-3-oxa-4-azapentylene)thymidine 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以70%的产率得到3'-C,4'-C-(3-oxa-4-azapentylene)thymidine
  参考文献：
  名称：

  Synthesis of a Novel trans-3’,4’-BNA Monomer Bearing a 4,8-Dioxa-5-azabicyclo[5.3.0]decane Skeleton

  摘要：

  A novel trans-3',4'-BNA monomer, in which sugar conformation was restricted to S-type by a trans-fused 3-oxa-4-azapentylene bridge between C3' and C4' position, was designed and synthesized. The trans-fused 7-membered cyclic structure within a 4,8-dioxa-5-azabicyclo[5.3.0]decane skeleton was prepared by means of intramolecular substitution reaction using potassium carbonate as a base. We found that all of protecting groups (benzyl, benzyloxymethyl, and benzyloxycarbonyl group) were able to be removed smoothly by DDQ oxidation followed by boron trichloride treatment without cleavage of N-O linkage to afford the desired trans-3',4'-BNA monomer.

  DOI：

  10.3987/com-08-s(d)58

文献信息

• Synthesis of a Novel trans-3’,4’-BNA Monomer Bearing a 4,8-Dioxa-5-azabicyclo[5.3.0]decane Skeleton
  作者：Satoshi Obika、Tetsuya Kodama、Kensaku Sugaya、Takeshi Baba、Takeshi Imanishi

  DOI：10.3987/com-08-s(d)58

  日期：——

  A novel trans-3',4'-BNA monomer, in which sugar conformation was restricted to S-type by a trans-fused 3-oxa-4-azapentylene bridge between C3' and C4' position, was designed and synthesized. The trans-fused 7-membered cyclic structure within a 4,8-dioxa-5-azabicyclo[5.3.0]decane skeleton was prepared by means of intramolecular substitution reaction using potassium carbonate as a base. We found that all of protecting groups (benzyl, benzyloxymethyl, and benzyloxycarbonyl group) were able to be removed smoothly by DDQ oxidation followed by boron trichloride treatment without cleavage of N-O linkage to afford the desired trans-3',4'-BNA monomer.