1-[(2R,4R,5S)-4-(hydroxymethyl)-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 146604-41-3

• 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: 1-[(2R,4R,5S)-4-(hydroxymethyl)-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 146604-41-3
• 化学式: C₃₀H₃₀N₂O₅
• 分子量: 498.579
• InChiKey: BHUCGCGUUALWLN-GDKKVTFASA-N

物化性质

• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(2R,4R,5S)-4-(hydroxymethyl)-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 氨 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 5'-O-dimethoxytrityl-3'-hydroxymethyl-3'-deoxy-thymidine
  参考文献：
  名称：

  5'-膦酸酯连接的胸苷脱氧寡核苷酸的合成

  摘要：

  合成了5'-脱氧-5'-膦基胸苷，并与3'-脱氧-3'-羟基-甲基胸苷偶联，得到3'-CO-5P-5'连接的胸苷二核苷酸。该二聚体作为其3'-亚磷酰胺被用于合成脱氧寡核苷酸。

  DOI：

  10.1016/0040-4039(96)01437-2
• 作为产物：
  描述：

  5'-O-tritylthymidine 在 sodium tetrahydroborate 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 1-[(2R,4R,5S)-4-(hydroxymethyl)-5-(trityloxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  5'-膦酸酯连接的胸苷脱氧寡核苷酸的合成

  摘要：

  合成了5'-脱氧-5'-膦基胸苷，并与3'-脱氧-3'-羟基-甲基胸苷偶联，得到3'-CO-5P-5'连接的胸苷二核苷酸。该二聚体作为其3'-亚磷酰胺被用于合成脱氧寡核苷酸。

  DOI：

  10.1016/0040-4039(96)01437-2

文献信息

• Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.
  作者：T. Kofoed、P. B. Rasmussen、P. Valentin-Hansen、E. B. Pedersen、Kari Rissanen、Wenjun Shi、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0318

  日期：——

  3'-Deoxy-3'-C-(hydroxymethyl)thymidine (3'-DHMT) and 5'-deoxy-5'-C-(hydroxymethyl)thymidine (5'-DHMT) have been prepared and used for the synthesis of novel oligodeoxynucleotides containing extended internucleotide linkages. Enzymatic stability toward exonuclease III degradation was studied and hybridization properties were tested, The extended 3'-homologous DNA causes complete cessation of exonuclease III degradation while the extended 5'-homologous DNA shows only same decrease in degradation. Duplexes having extended internucleotide linkages show a minor decrease in hybridization stability. Tripler formation with 20-mer duplexes at pH 5.5 and high salt concentration gave almost no decrease in binding affinity when compared with unmodified tripler formation. UV experiments were also performed with oligodeoxynucleotides containing hairpin structures and bulged bases, Extended linkages in the oligodeoxynucleotides gave a small increase in T-m with sequences containing a loop, but no change or only a small decrease was observed when an extra thymidine nucleotide was incorporated in the complementary strand.
• EP0586570A4
  申请人：——

  公开号：EP0586570A4

  公开（公告）日：1996-01-24
• BACKBONE MODIFIED OLIGONUCLEOTIDE ANALOGUES
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0586570A1

  公开（公告）日：1994-03-16
• US5386023A
  申请人：——

  公开号：US5386023A

  公开（公告）日：1995-01-31
• US5489677A
  申请人：——

  公开号：US5489677A

  公开（公告）日：1996-02-06