(1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-1-carboxylic acid | 156043-96-8

• 分子结构分类: 有机化合物
• 英文名称: (1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-1-carboxylic acid
• 英文别名: (1S,3S,4R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]bicyclo[3.1.0]hexane-1-carboxylic acid
• CAS: 156043-96-8
• 化学式: C₂₀H₄₀O₄Si₂
• 分子量: 400.706
• InChiKey: NXJCEWFRIHMYLL-ULMVMLMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-1-carboxylic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.25h， 生成 [(1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hex-1-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  1′,6′-methano carbocyclic thymidine: Synthesis, x-ray crystal structure, and effect on nucleic acid duplex stability

  摘要：

  The title compound 1 has been synthesized via bicyclic lactone 3 and amine 9 as the key intermediates. X-ray crystallography reveals the bicyclic skeleton of 1 to adopt a boat-like (3'exo) conformation. Oligodeoxyribonucleotides incorporating up to 10 building blocks 1 in place of natural thymidine are still capable of binding to complementary DNA or RNA, albeit with lower affinity than the unmodified parent compounds.

  DOI：

  10.1016/s0040-4039(00)78359-6
• 作为产物：
  描述：

  (1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以78%的产率得到(1S,3S,4R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-1-carboxylic acid
  参考文献：
  名称：

  1′,6′-methano carbocyclic thymidine: Synthesis, x-ray crystal structure, and effect on nucleic acid duplex stability

  摘要：

  The title compound 1 has been synthesized via bicyclic lactone 3 and amine 9 as the key intermediates. X-ray crystallography reveals the bicyclic skeleton of 1 to adopt a boat-like (3'exo) conformation. Oligodeoxyribonucleotides incorporating up to 10 building blocks 1 in place of natural thymidine are still capable of binding to complementary DNA or RNA, albeit with lower affinity than the unmodified parent compounds.

  DOI：

  10.1016/s0040-4039(00)78359-6