(2R,3aS,5R,6aR)-2-methoxy-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3a,5-diol | 1443136-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3aS,5R,6aR)-2-methoxy-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3a,5-diol
• CAS: 1443136-90-0
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: VFMPKDUZUHNDBN-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.37
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3aS,5R,6aR)-2-methoxy-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3a,5-diol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82%的产率得到
  参考文献：
  名称：

  Synthesis and Properties of Isobicyclo-DNA

  摘要：

  AbstractWe present the synthesis of the isobicyclo‐DNA building blocks with the nucleobases A, C, G and T, as well as biophysical and biological properties of oligonucleotides derived thereof. The synthesis of the sugar part was achieved in 5 steps starting from a known intermediate of the tricyclo‐DNA synthesis. Dodecamers containing single isobicyclo‐thymidine incorporations, fully modified A‐ and T‐containing sequences, and fully modified oligonucleotides containing all four bases were synthesized and characterized. Isobicyclo‐DNA forms stable duplexes with natural nucleic acids with a pronounced preference for DNA over RNA as complements. The most stable duplexes, however, arise by self‐pairing. Isobicyclo‐DNA forms preferentially B‐DNA‐like duplexes with DNA and A‐like duplexes with complementary RNA as determined by circular dichroism (CD) spectroscopy. Self‐paired duplexes show a yet unknown structure, as judged from CD spectroscopy. Biochemical tests revealed that isobicyclo‐DNA is stable in fetal bovine serum and does not elicit RNaseH activity.

  DOI：

  10.1002/chem.201300487
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(2R,3aS,5R,6aR)-2-methoxy-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3a,5-diol
  参考文献：
  名称：

  Synthesis and Properties of Isobicyclo-DNA

  摘要：

  AbstractWe present the synthesis of the isobicyclo‐DNA building blocks with the nucleobases A, C, G and T, as well as biophysical and biological properties of oligonucleotides derived thereof. The synthesis of the sugar part was achieved in 5 steps starting from a known intermediate of the tricyclo‐DNA synthesis. Dodecamers containing single isobicyclo‐thymidine incorporations, fully modified A‐ and T‐containing sequences, and fully modified oligonucleotides containing all four bases were synthesized and characterized. Isobicyclo‐DNA forms stable duplexes with natural nucleic acids with a pronounced preference for DNA over RNA as complements. The most stable duplexes, however, arise by self‐pairing. Isobicyclo‐DNA forms preferentially B‐DNA‐like duplexes with DNA and A‐like duplexes with complementary RNA as determined by circular dichroism (CD) spectroscopy. Self‐paired duplexes show a yet unknown structure, as judged from CD spectroscopy. Biochemical tests revealed that isobicyclo‐DNA is stable in fetal bovine serum and does not elicit RNaseH activity.

  DOI：

  10.1002/chem.201300487