5'-deoxy-5'-bromo-3'-O-acetylthymidine | 34647-05-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 5'-deoxy-5'-bromo-3'-O-acetylthymidine
• 英文别名: O^3'-acetyl-5'-bromo-5'-deoxy-thymidine
• CAS: 34647-05-7
• 化学式: C₁₂H₁₅BrN₂O₅
• 分子量: 347.166
• InChiKey: QZGHEIXSUPNYFW-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  90.39
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  sodium 2-mercaptoethanol 、 5'-deoxy-5'-bromo-3'-O-acetylthymidine 以 乙醇 为溶剂， 反应 0.25h， 以18 mg的产率得到5'-deoxy-5'-(2-hydroxyethylthio)thymidine
  参考文献：
  名称：

  Diastereomers of Nucleoside 3'-O-(2-Thio-1,3,2-oxathia(selena)phospholanes): Building Blocks for Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s

  摘要：

  Diastereomerically pure 5'-O-DMT-nucleoside 3'-O-(2-thio-1,3,2-oxathiaphospholanes) (3) and their oxathiaphospholane ring-substituted analogues (20) were used for the synthesis of stereoregular oligo(nucleoside phosphorothioate)s (S-Oligos). The oxathiaphospholane ring-opening condensation requires the presence of strong organic base, preferably DBU. The yield of a single coupling step is ca. 95% and resulting S-Oligos are free of nucleobase- and sugar-phosphorothioate backbone modifications. The diastereomeric purity of products was estimated on the basis of diastereoselective degradation with Nuclease P1 and a mixture of snake venom phosphodiesterase and Serratia marcescens endonuclease. Thermal dissociation studies of heteroduplexes S-Oligos/DNA and S-Oligos/RNA showed that their stability is stereochemistry- and sequence-dependent.

  DOI：

  10.1021/ja00154a001