5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoylthymidine | 905435-92-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoylthymidine
• 英文别名: [3-[[(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy]-2-benzoyloxypropyl] benzoate
• CAS: 905435-92-9
• 化学式: C₃₄H₃₂N₂O₁₀
• 分子量: 628.635
• InChiKey: SVUTTWDEEDAVMP-WGAJCZKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoylthymidine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 二氯特诺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoylthymidine 3'-O-(2-cyanoethyl-N,N'-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Synthesis and Application of a 5‘-Aldehyde Phosphoramidite for Covalent Attachment of DNA to Biomolecules

  摘要：

  We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5'-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5'-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5'-aldehyde-DNA with 2'-amino-2'-deoxyRNA. These procedures should be generally applicable for attaching DNA to biomolecules.

  DOI：

  10.1021/jo060723m
• 作为产物：
  描述：

  beta-胸苷 在 palladium on activated charcoal 吡啶 、 AD-mix-β 、 氢气 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 3.75h， 生成 5'-O-(2,3-di-O-benzoylpropyl)-N³-benzoylthymidine
  参考文献：
  名称：

  Synthesis and Application of a 5‘-Aldehyde Phosphoramidite for Covalent Attachment of DNA to Biomolecules

  摘要：

  We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5'-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5'-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5'-aldehyde-DNA with 2'-amino-2'-deoxyRNA. These procedures should be generally applicable for attaching DNA to biomolecules.

  DOI：

  10.1021/jo060723m

文献信息

• Synthesis and Application of a 5‘-Aldehyde Phosphoramidite for Covalent Attachment of DNA to Biomolecules
  作者：Chandrasekhar V. Miduturu、Scott K. Silverman

  DOI：10.1021/jo060723m

  日期：2006.7.1

  We recently reported the use of covalently attached DNA as a structural constraint for rational control of macromolecular conformation. Reductive amination was employed to attach each strand of the duplex DNA constraint to RNA, utilizing an aldehyde tethered to the 5'-terminus of the DNA. Here we describe the synthesis of a thymidine phosphoramidite that has the 5'-tethered aldehyde masked as a 1,2-diol. We also describe optimized reductive amination conditions for linking 5'-aldehyde-DNA with 2'-amino-2'-deoxyRNA. These procedures should be generally applicable for attaching DNA to biomolecules.