5'-O-phthalimido-3'-t-butyldiphenylsilylthymidine | 140659-86-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-phthalimido-3'-t-butyldiphenylsilylthymidine
• 英文别名: 5'-O-phthalimido-3'-O-(t-butyldiphenylsilyl)thymidine；5'-O-phthalimido-3'-O-tert-butyl(diphenyl)silylthymidine；3'-O-(t-butyldiphenylsilyl)-5'-O-phthalimidothymidine；2-[[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]isoindole-1,3-dione
• CAS: 140659-86-5
• 化学式: C₃₄H₃₅N₃O₇Si
• 分子量: 625.753
• InChiKey: QHZPOOBZMAHKRT-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-phthalimido-3'-t-butyldiphenylsilylthymidine 在 甲基肼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 5'-O-(methyleneamino)-3'-(t-butyldiphenylsilyl)thymidine
  参考文献：
  名称：

  Intermolecular radical CC bond formation: Synthesis of a novel dinucleoside linker for non-anionic antisense oligonucleosides

  摘要：

  An efficient, stereoselective synthesis of a thymidine (T) nucleoside dimer (T-3'-CH2-NH-O-5'-T) 1 has been accomplished via an intermolecular radical reaction. The new dimer and methodology is useful for the development of backbone modified antisense oligonucleosides.

  DOI：

  10.1016/s0040-4039(00)79047-2
• 作为产物：
  描述：

  beta-胸苷 、 alkaline earth salt of/the/ methylsulfuric acid 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5'-O-phthalimido-3'-t-butyldiphenylsilylthymidine
  参考文献：
  名称：

  Oligonucleosides: synthesis of a novel methylhydroxylamine-linked nucleoside dimer and its incorporation into antisense sequences

  摘要：

  DOI：

  10.1021/ja00036a076

文献信息

• Backbone modified oligonucleotide analogs
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US05378825A1

  公开（公告）日：1995-01-03

  Therapeutic oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in wild type oligomers with four atom linking groups forms unique di- and poly- nucleosides and nucleotides useful in regulating RNA expression and in therapeutics. Methods of synthesis and use are also disclosed.

  提供了具有改善核酸酶抗性和细胞摄取能力的治疗性寡核苷酸类似物。用四个原子连接基取代野生型寡聚物中发现的正常磷酸二酯间糖连接，形成独特的二核苷酸和多核苷酸，可用于调节RNA表达和治疗。还公开了合成和使用的方法。
• Backbone modified oligonucleotide analogs and preparation thereof
  申请人：Isis Pharmaceuticals

  公开号：US05386023A1

  公开（公告）日：1995-01-31

  Methods for preparing oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. In preferred embodiments, the methods involve reductive coupling of 3'- and 4'-substituted or 4'- and 3'-substituted nucleosidic synthons.

  提供了制备寡核苷酸类似物的方法，这些类似物具有改善的核酸酶抗性和改善的细胞摄取能力。在优选实施例中，该方法涉及3'-和4'-取代或4'-和3'-取代的核苷合成物的还原偶联。
• Backbone-modified oligonucleotide analogs and methods for using same
  申请人：——

  公开号：US20020183502A1

  公开（公告）日：2002-12-05

  Therapeutic oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. Replacement of phosphorodiester inter-sugar linkages found in wild type oligomers with four atom linking groups forms unique di- and poly-nucleosides and nucleotides useful in regulating RNA expression and in therapeutics. Methods of synthesis and use are also disclosed.

  本发明提供了具有改良核酸酶抵抗性和改良细胞摄取能力的治疗性寡核苷酸类似物。通过用四原子连接基取代野生型寡聚物中发现的磷酸二酯间糖连接，形成独特的二核苷酸和多核苷酸，可用于调节RNA表达和治疗。还公开了合成和使用的方法。
• Backbone-modified oligonucleotide analogs and preparation thereof
  申请人：ISIS Pharmacueticals, Inc.

  公开号：US05618704A1

  公开（公告）日：1997-04-08

  Methods for preparing oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. In preferred embodiments, the methods involve radical coupling of 3'- and 5'-substituted or 5'- and 3'-substituted nucleosidic synthons.

  提供了制备寡核苷酸类似物的方法，这些类似物具有改善的核酸酶抗性和改善的细胞摄取能力。在优选实施方式中，该方法涉及3'-和5'-取代或5'-和3'-取代的核苷酸合成物的自由基偶联。
• Backbone modified oligonucleotide analogues
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US05610289A1

  公开（公告）日：1997-03-11

  Therapeutic oligonucleotide analogues which have improved nuclease resistance and improved cellular uptake are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligomers with four atom linking groups forms unique di- and poly- nucleosides and nucleotides useful in regulating RNA expression and in therapeutics. Methods of synthesis and use are also disclosed.

  本发明提供了具有改善核酸酶抵抗力和改善细胞摄取的治疗性寡核苷酸类似物。通过用四个原子连接基替换天然寡聚物中的正常磷酸二酯间糖链，形成独特的二核苷酸和多核苷酸，可用于调节RNA表达和治疗。还公开了合成和使用方法。