5'-O-allyl-3'-O-benzylthymidine | 905435-89-4

• 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-allyl-3'-O-benzylthymidine
• 英文别名: 5-methyl-1-[(2R,4S,5R)-4-phenylmethoxy-5-(prop-2-enoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 905435-89-4
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: OPTRYSRSXPUZTC-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-O-allyl-3'-O-benzylthymidine 在 palladium on activated charcoal 吡啶 、 AD-mix-β 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 1.75h， 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
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5'-O-allyl-3'-O-benzylthymidine
  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.