3',5'-di-O-benzyl-3'-C,4'-C-(N-benzyloxycarbonyl-3-oxa-4-azapentylene)-3-N-benzyloxymethylthymidine | 1161846-18-9

• 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: 3',5'-di-O-benzyl-3'-C,4'-C-(N-benzyloxycarbonyl-3-oxa-4-azapentylene)-3-N-benzyloxymethylthymidine
• 英文别名: benzyl (2R,3aS,8aR)-2-[5-methyl-2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]-3a-phenylmethoxy-8a-(phenylmethoxymethyl)-3,4,5,8-tetrahydro-2H-furo[2,3-d]oxazepine-7-carboxylate
• CAS: 1161846-18-9
• 化学式: C₄₃H₄₅N₃O₉
• 分子量: 747.845
• InChiKey: FSWKGZKHUBDWNW-SMIPYKAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-benzyl-3'-C,4'-C-(N-benzyloxycarbonyl-3-oxa-4-azapentylene)-3-N-benzyloxymethylthymidine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以57%的产率得到3'-C,4'-C-(N-benzyloxycarbonyl-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
• 作为产物：
  描述：

  3',5'-di-O-benzyl-3'-C-[2-(N-benzyloxycarbonylaminoxy)ethyl]-3-N-benzyloxymethyl-4'-C-(tosyloxymethyl)thymidine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以67%的产率得到3',5'-di-O-benzyl-3'-C,4'-C-(N-benzyloxycarbonyl-3-oxa-4-azapentylene)-3-N-benzyloxymethylthymidine
  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