[(2R,4aR,7S,8S,8aS)-4a-ethenyl-8-(4-methylphenyl)sulfonyloxy-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate | 1180502-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,4aR,7S,8S,8aS)-4a-ethenyl-8-(4-methylphenyl)sulfonyloxy-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate
• CAS: 1180502-80-0
• 化学式: C₂₉H₃₀O₉S₂
• 分子量: 586.684
• InChiKey: REDTWMPSPIRYJH-XPLNXOJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,7S,8S,8aS)-4a-ethenyl-8-(4-methylphenyl)sulfonyloxy-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate 在 sodium tetrahydroborate 、 sodium methylate 、 sodium hydride 、 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 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 33.33h， 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 、 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 为溶剂， 反应 151.0h， 生成 [(2R,4aR,7S,8S,8aS)-4a-ethenyl-8-(4-methylphenyl)sulfonyloxy-2-phenyl-6,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate
  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.