5'-N-trifluoroacetyl-N-(2-hydroxyethyl)-3'-O-t-butyldimethylsilyl-5'-deoxy-5'-aminothymidine | 405157-17-7

• 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'-N-trifluoroacetyl-N-(2-hydroxyethyl)-3'-O-t-butyldimethylsilyl-5'-deoxy-5'-aminothymidine
• 英文别名: N-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]-2,2,2-trifluoro-N-(2-hydroxyethyl)acetamide
• CAS: 405157-17-7
• 化学式: C₂₀H₃₂F₃N₃O₆Si
• 分子量: 495.571
• InChiKey: KESUEERSVJXQGH-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 5'-N-trifluoroacetyl-N-(2-hydroxyethyl)-3'-O-t-butyldimethylsilyl-5'-deoxy-5'-aminothymidine 在 吡啶 作用下， 反应 8.0h， 以83%的产率得到N-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethyl]-N-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage

  摘要：

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01034-1
• 作为产物：
  描述：

  5-O-(4-甲基苯基磺酰基)胸腺嘧啶脱氧核苷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 5'-N-trifluoroacetyl-N-(2-hydroxyethyl)-3'-O-t-butyldimethylsilyl-5'-deoxy-5'-aminothymidine
  参考文献：
  名称：

  Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage

  摘要：

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01034-1

文献信息

• Oligodeoxynucleotides with extended zwitter-ionic internucleotide linkage
  作者：Svetlana V Kochetkova、Edward N Timofeev、Ekaterina A Korobeinikova、Natalia A Kolganova、Vladimir L Florentiev

  DOI：10.1016/s0040-4020(01)01034-1

  日期：2001.12

  Two non-natural nucleoside analogues, N-(2-hydroxyethyl)-2',5'-dideoxy-5'-aminothymidine (dT(NH)) and N-(2-hydroxyethyl)N-methyl-2,5'-dideoxy-5'-aminothymidine (dT(NMe)), have been prepared and used in the synthesis of oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides, modified at internucleotide linkages. Both modified oligodeoxythymidilates and mixed-sequence oligodeoxynucleotides have been shown to form zwitter-ionic phosphate-amine pairs as evidenced by their decreased electrophoretic mobility in denaturing polyacrylamide gel. (C) 2001 Elsevier Science Ltd. All rights reserved.