5'-O-dimethoxytrityl-α-thymidine | 104766-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-dimethoxytrityl-α-thymidine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine；1-[(2S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 104766-16-7
• 化学式: C₃₁H₃₂N₂O₇
• 分子量: 544.604
• InChiKey: UBTJZUKVKGZHAD-IARZGTGTSA-N

物化性质

• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112.01
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-α-thymidine 在 吡啶 、 咪唑 、 氨 、 三乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 39.0h， 生成 5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-5-methyl-2'-deoxy-α-cytidine
  参考文献：
  名称：

  Oligo-α-deoxyribonucleotides with a modified nucleic base and covalently linked to reactive agents

  摘要：

  Solid-phase preparation of oligo-alpha-deoxyribonucleotides attached to intercalator, chemically or photochemically reactive groups through either their 5'- or 3'-ends, including use of the 5-methyl-alpha-deoxycytidine.

  DOI：

  10.1016/s0040-4020(01)87973-4
• 作为产物：
  描述：

  Alpha-胸苷 生成 5'-O-dimethoxytrityl-α-thymidine
  参考文献：
  名称：

  Novel DNA Analog for Potential Gene Regulating Agent. A Convenient Synthesis of α-Oligodeoxyribonucleotide Phosphorothioate Bearing 3′-Monophosphate

  摘要：

  利用附着在聚四氟乙烯基固体支持物上的核糖腺苷，通过亚磷酰胺法方便地合成了含 3′-单磷酸的α-2′-去氧肌酸硫代磷酸酯类似物。所获得的寡聚体对常见核酸酶的消化具有更高的稳定性。

  DOI：

  10.1246/cl.1991.1941

文献信息

• 5'-END DERIVATIVES
  申请人：Manoharan Muthiah

  公开号：US20130323836A1

  公开（公告）日：2013-12-05

  The present invention provides compounds of formula (1). Another aspect of the invention relates to a method of inhibiting the expression of a gene in call, the method comprising (a) contacting an oligonucleotide of the invention with the cell; and (b) maintaining the cell from step (a) for a time sufficient to obtain degradation of the mRNA of the target gene.

  本发明提供了式（1）的化合物。发明的另一个方面涉及抑制细胞中基因表达的方法，该方法包括（a）将本发明的寡核苷酸与细胞接触；以及（b）维持从步骤（a）中的细胞足够时间以获得目标基因mRNA的降解。
• Improved Targeting of the Flanks of a DNA Stem Using α-Oligodeoxynucleotides.-The Enhanced Effect of an Intercalator
  作者：Ahmed F. Khattab、Erik B. Pedersen

  DOI：10.1080/07328319808004323

  日期：1998.12

  2'-Deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 3 which was synthesized from 5-O-DMT protected alpha-thymidine 1. Aminolysis of 3 afforded 3'-O-acetyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (8). Benzoylation of 8 and removal of acetyl afforded N-4-benzoyl-(2)-deoxy-5-O-(4,4'-dimethoxytrityl)-5-methyl-alpha-cytidine (10). The amidites of compounds 5 and 10 were prepared and used in ol-oligonucleotide synthesis. DNA three-way junction (TWJ) is stabilized when an alpha-ODN is used for targeting the dangling flanks of the stem in a DNA hairpin. Further stabilization of the TWJ is observed when 5 is inserted into the alpha-ODN at the junction region.