5'-O-Amino-N⁴-benzoyl-2'-deoxycytidine | 166758-11-8

• 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-Amino-N⁴-benzoyl-2'-deoxycytidine
• 英文别名: N-[1-[(2R,4S,5R)-5-(aminooxymethyl)-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 166758-11-8
• 化学式: C₁₆H₁₈N₄O₅
• 分子量: 346.343
• InChiKey: XYDSCAFCKZGIRZ-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷	4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine	67219-55-0	C37H35N3O7	633.701
  ——	5'-O-Amino-N4-benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxycytidine	166758-10-7	C32H36N4O5Si	584.747
  ——	3'-O-tert-butydiphenylsilyl-N4-benzoyl-2'-deoxycytidine	166758-08-3	C32H35N3O5Si	569.732
  ——	N4-Benzoyl-3'-O-(tert-butyldiphenylsilyl)-2'-deoxy-5'-O-phthalimidocytidine	166758-09-4	C40H38N4O7Si	714.85
  ——	4-N-benzoyl-2'-deoxy-3'-O-tert-butyldiphenylsilyl-5'-O-dimethoxytritylcytidine	166758-07-2	C53H53N3O7Si	872.105

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5'-O-Amino-2'-deoxycytidine	——	C9H14N4O4	242.235

反应信息

• 作为反应物：
  描述：

  5'-O-Amino-N⁴-benzoyl-2'-deoxycytidine 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以45%的产率得到5'-O-Amino-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：

  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 咪唑 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 三苯基膦 、 甲基肼 、 三氯乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 5'-O-Amino-N⁴-benzoyl-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

文献信息

• 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.