1-[(2R,4aR,7R,8S,8aS)-8-hydroxy-4a-(hydroxymethyl)-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl]-5-methylpyrimidine-2,4-dione | 1180502-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-[(2R,4aR,7R,8S,8aS)-8-hydroxy-4a-(hydroxymethyl)-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1180502-88-8
• 化学式: C₁₉H₂₂N₂O₇
• 分子量: 390.393
• InChiKey: ZCECBKUVFVEUAK-LEVYEWFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,4aR,7R,8S,8aS)-8-hydroxy-4a-(hydroxymethyl)-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 咪唑 、 N-甲基咪唑 、 四氮唑 、 水 、 sodium hydride 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 38.25h， 生成
  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 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 氨 、 水 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 184.33h， 生成 1-[(2R,4aR,7R,8S,8aS)-8-hydroxy-4a-(hydroxymethyl)-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl]-5-methylpyrimidine-2,4-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

文献信息

• US8530640B2
  申请人：——

  公开号：US8530640B2

  公开（公告）日：2013-09-10
• 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.