(((3aR,3bR,4aS,5R,5aS)-5-azido-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-3b(3aH)-yl)methoxy)(tert-butyl)diphenylsilane | 1309375-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (((3aR,3bR,4aS,5R,5aS)-5-azido-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-3b(3aH)-yl)methoxy)(tert-butyl)diphenylsilane
• CAS: 1309375-15-2
• 化学式: C₂₆H₃₃N₃O₃Si
• 分子量: 463.652
• InChiKey: ZYMAXMNOXRIDSP-IOCWQACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  76.45
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (((3aR,3bR,4aS,5R,5aS)-5-azido-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-3b(3aH)-yl)methoxy)(tert-butyl)diphenylsilane 在 吡啶 、 盐酸 、 三甲基氯硅烷 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 41.92h， 生成
  参考文献：
  名称：

  A Direct, Efficient Method for the Preparation of siRNAs Containing Ribo-like North Bicyclo[3.1.0]hexane Pseudosugars

  摘要：

  An efficient method for the preparation of siRNAs modified with ribo-like North bicyclo[3.1.0]hexane pseudosugars is described. The combined use of 2'-O-(2-cyanoethoxymethyl) (CEM) and 2'-O-TBDMS protection was successfully employed for RNA synthesis with the added advantage that both groups were efficiently removed in a single step. The resulting North ribo-methanocarba-modified siRNAs are compatible with the intracellular RNAi machinery and can mediate specific degradation of target mRNA.

  DOI：

  10.1021/ol200909j
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86.1%的产率得到(((3aR,3bR,4aS,5R,5aS)-5-azido-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-3b(3aH)-yl)methoxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  A Direct, Efficient Method for the Preparation of siRNAs Containing Ribo-like North Bicyclo[3.1.0]hexane Pseudosugars

  摘要：

  An efficient method for the preparation of siRNAs modified with ribo-like North bicyclo[3.1.0]hexane pseudosugars is described. The combined use of 2'-O-(2-cyanoethoxymethyl) (CEM) and 2'-O-TBDMS protection was successfully employed for RNA synthesis with the added advantage that both groups were efficiently removed in a single step. The resulting North ribo-methanocarba-modified siRNAs are compatible with the intracellular RNAi machinery and can mediate specific degradation of target mRNA.

  DOI：

  10.1021/ol200909j