5'-O-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine | 158813-59-3

• 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-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[tert-butyl(diphenyl)silyl]oxyoxolan-2-yl]-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
• CAS: 158813-59-3
• 化学式: C₃₄H₄₇N₅O₄Si₂
• 分子量: 645.949
• InChiKey: YRDNKWPYWBSEJY-FRXPANAUSA-N

物化性质

• 沸点：
  676.8±65.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine 在 TMSTf 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 5'-O-Phthalimido-N⁴-benzoyl-3'-O-(tert-butyldiphenylsilyl)-5-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 咪唑 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5'-O-(tert-Butyldimethylsilyl)-3'-O-(tert-butyldiphenylsilyl)-4-(1,2,4-triazolyl)thymidine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037

文献信息

• Perbost, Michel; Sanghvi, Yogesh S., Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2051 - 2052
  作者：Perbost, Michel、Sanghvi, Yogesh S.

  DOI：——

  日期：——
• Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides
  作者：Michel Perbost、Tomonori Hoshiko、Francois Morvan、Eric Swayze、Richard H. Griffey、Yogesh S. Sanghvi

  DOI：10.1021/jo00121a037

  日期：1995.8

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.