5'-deoxy-5'-(2-hydroxyethylthio)thymidine | 70465-78-0

• 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'-(2-hydroxyethylthio)thymidine
• 英文别名: 1-[(2R,4S,5S)-4-hydroxy-5-(2-hydroxyethylsulfanylmethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 70465-78-0
• 化学式: C₁₂H₁₈N₂O₅S
• 分子量: 302.351
• InChiKey: FNGQBMRJRHJJLC-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5'-(2-hydroxyethylthio)thymidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 生成 3'-O-(P-β-cyanoethoxy-N,N-diisopropylaminophosphinyl)-5'-deoxy-5'-(2-O-4,4'-dimethoxytritylethylthio)thymidine
  参考文献：
  名称：

  Synthesis of triple helix forming oligonucleotides with a stretched phosphodiester backbone

  摘要：

  DOI：

  10.1016/s0040-4039(00)73706-3
• 作为产物：
  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

文献信息

• Synthesis of triple helix forming oligonucleotides with a stretched phosphodiester backbone
  作者：T. Sudhakar Rao、K. Jayaraman、Ganapathi R. Revankar

  DOI：10.1016/s0040-4039(00)73706-3

  日期：1993.9
• Diastereomers of Nucleoside 3'-O-(2-Thio-1,3,2-oxathia(selena)phospholanes): Building Blocks for Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s
  作者：Wojciech J. Stec、Andrzej Grajkowski、Anna Kobylanska、Boleslaw Karwowski、Maria Koziolkiewicz、Konrad Misiura、Andrzej Okruszek、Andrzej Wilk、Piotr Guga、Malgorzata Boczkowska

  DOI：10.1021/ja00154a001

  日期：1995.12

  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.
• Synthesis of Triple Helix Forming Oligonucleotides with a Stretched Phosphodiester Backbone
  作者：T. Sudhakar Rao、Krishna Jayaraman、Ross H. Durland、Ganapathi R. Revankar

  DOI：10.1080/15257779408013239

  日期：1994.3

  Total synthesis of novel DMT-phosphoramidites of thymidine (11 and 15) and 2'-deoxyguanosine (8 and 20) have been accomplished. The utility of these modified building blocks in the preparation of triple helix forming oligodeoxyribonucleotides with a stretched phosphodiester backbone has been evaluated. It was found that the oligonucleotides with extended backbones were unable to enhance the binding to duplex targets containing CG or TA base pairs.