1-(3'-O-amino-2'-deoxy-5'-O-tert-butyldimethylsilyl-β-D-threo-pentofuranosyl)thymine | 161424-61-9

• 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: 1-(3'-O-amino-2'-deoxy-5'-O-tert-butyldimethylsilyl-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5R)-4-aminooxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 161424-61-9
• 化学式: C₁₆H₂₉N₃O₅Si
• 分子量: 371.509
• InChiKey: CLUYTKSTZWHIBN-JHJVBQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.57
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(3'-O-amino-2'-deoxy-5'-O-tert-butyldimethylsilyl-β-D-threo-pentofuranosyl)thymine 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.17h， 生成 1-<2',3',5'-trideoxy-3',5'-(epoxy(N-ethoxycarbonyl)imino)-β-D-threo-pentofuranosyl>thymine
  参考文献：
  名称：

  Novel Types of Bicyclonucleosides: Isoxazolidinofuranosylthymines

  摘要：

  Novel types of bicyclonucleosides (3, 9) bearing a 3',5'-epoxyimino (or iminoepoxy) bridge have been prepared using intramolecular Mitsunobu reactions. Contrarily to close analogs, also of the beta-D-threo configuration but oxidizable to nitrones (2, 2') which were found active against HIV, the new compounds exhibited no anti-HIV activity.

  DOI：

  10.1080/15257779408013208
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.67h， 生成 1-(3'-O-amino-2'-deoxy-5'-O-tert-butyldimethylsilyl-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Novel Types of Bicyclonucleosides: Isoxazolidinofuranosylthymines

  摘要：

  Novel types of bicyclonucleosides (3, 9) bearing a 3',5'-epoxyimino (or iminoepoxy) bridge have been prepared using intramolecular Mitsunobu reactions. Contrarily to close analogs, also of the beta-D-threo configuration but oxidizable to nitrones (2, 2') which were found active against HIV, the new compounds exhibited no anti-HIV activity.

  DOI：

  10.1080/15257779408013208

文献信息

• Synthesis of a New Hydroxyamino Linked Thymidine Dimer via a Radical C-C Bond Formation
  作者：Yogesh Sanghvi、P. Dan Cook

  DOI：10.1080/15257779508012489

  日期：1995.5.1

  Abstract An efficient synthesis of a thymidine nucleoside dimer [T-3′-β-O-N(CH3)-CH2-5′-T] has been accomplished via an intermolecular radical coupling reaction. The novel dimer contains an achiral and neutral backbone linkage which may have potential application in constructing backbone modified antisense oligonucleosides.

  摘要通过分子间自由基偶联反应，成功合成了胸苷核苷二聚体[T-3'-β-ON（CH3）-CH2-5'-T]。新型二聚体包含非手性和中性主链连接，在构建主链修饰的反义寡核苷中可能具有潜在的应用。
• Novel Types of Bicyclonucleosides: Isoxazolidinofuranosylthymines
  作者：J. M. J. Tronchet、M. Zsely、N. Sultan

  DOI：10.1080/15257779408013208

  日期：1994.12

  Novel types of bicyclonucleosides (3, 9) bearing a 3',5'-epoxyimino (or iminoepoxy) bridge have been prepared using intramolecular Mitsunobu reactions. Contrarily to close analogs, also of the beta-D-threo configuration but oxidizable to nitrones (2, 2') which were found active against HIV, the new compounds exhibited no anti-HIV activity.