(1S,2S,4S,7R,10R)-7-ethenyl-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane | 1180502-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1S,2S,4S,7R,10R)-7-ethenyl-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane
• CAS: 1180502-63-9
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: KVQAZJZJSSKOCT-BTFPBAQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4S,7R,10R)-7-ethenyl-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane 在 sodium tetrahydroborate 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 1-((2R,4aR,7R,8S,8aS)-8-hydroxy-4a-(hydroxymethyl)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Biophysical Properties of Constrained d-Altritol Nucleic Acids (cANA)

  摘要：

  The first synthesis of constrained altritol nucleic acids (cANA) containing antisense oligonucleotides (ASOs) was carried out to ascertain how conformationally restricting the D-altritol backbone-containing ASO (Me-ANA) would affect their ability to form duplexes with RNA. It was found that the thermal stability was reduced (cANA/RNA 1.1 degrees C/modification) compared to DNA/RNA, suggesting the constrained system results in a small destabilizing perturbation in the duplex structure.

  DOI：

  10.1021/ol401730d
• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 偶氮二异丁腈 、 氨 、 水 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 176.0h， 生成 (1S,2S,4S,7R,10R)-7-ethenyl-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane
  参考文献：
  名称：

  Synthesis and Biophysical Properties of Constrained d-Altritol Nucleic Acids (cANA)

  摘要：

  The first synthesis of constrained altritol nucleic acids (cANA) containing antisense oligonucleotides (ASOs) was carried out to ascertain how conformationally restricting the D-altritol backbone-containing ASO (Me-ANA) would affect their ability to form duplexes with RNA. It was found that the thermal stability was reduced (cANA/RNA 1.1 degrees C/modification) compared to DNA/RNA, suggesting the constrained system results in a small destabilizing perturbation in the duplex structure.

  DOI：

  10.1021/ol401730d

文献信息

• BICYCLIC CYCLOHEXITOL NUCLEIC ACID ANALOGS
  申请人：Seth Punit P.

  公开号：US20110077390A1

  公开（公告）日：2011-03-31

  The present disclosure provides bicyclic cyclohexitol nucleoside analogs of formula I and oligomeric compounds comprising these nucleoside analogs. These bicyclic nucleoside analogs are expected to be useful for enhancing properties of oligomeric compounds including for example nuclease resistance.
• US8530640B2
  申请人：——

  公开号：US8530640B2

  公开（公告）日：2013-09-10
• [EN] BICYCLIC CYCLOHEXITOL NUCLEIC ACID ANALOGS<br/>[FR] ANALOGUES D'ACIDES NUCLÉIQUES DE CYCLOHEXITOL BICYCLIQUES
  申请人：ISIS PHARMACEUTICALS INC

  公开号：WO2009100320A2

  公开（公告）日：2009-08-13

  The present disclosure provides bicyclic cyclohexitol nucleoside analogs of formula I and oligomeric compounds comprising these nucleoside analogs. These bicyclic nucleoside analogs are expected to be useful for enhancing properties of oligomeric compounds including for example nuclease resistance.
• Synthesis and Biophysical Properties of Constrained <scp>d</scp>-Altritol Nucleic Acids (cANA)
  作者：Michael T. Migawa、Thazha P. Prakash、Guillermo Vasquez、Punit P. Seth、Eric E. Swayze

  DOI：10.1021/ol401730d

  日期：2013.9.6

  The first synthesis of constrained altritol nucleic acids (cANA) containing antisense oligonucleotides (ASOs) was carried out to ascertain how conformationally restricting the D-altritol backbone-containing ASO (Me-ANA) would affect their ability to form duplexes with RNA. It was found that the thermal stability was reduced (cANA/RNA 1.1 degrees C/modification) compared to DNA/RNA, suggesting the constrained system results in a small destabilizing perturbation in the duplex structure.