N⁴-benzoyl-3',5'-O-dimesyl-2'-deoxycytidine | 124616-27-9

• 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: N⁴-benzoyl-3',5'-O-dimesyl-2'-deoxycytidine
• 英文别名: N4-benzoyl-3',5'-di-O-mesyl-2'-deoxycytidine；[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl methanesulfonate
• CAS: 124616-27-9
• 化学式: C₁₈H₂₁N₃O₉S₂
• 分子量: 487.511
• InChiKey: HFBCERYJWAHIRX-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁴-benzoyl-3',5'-O-dimesyl-2'-deoxycytidine 在 potassium phtalimide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以60%的产率得到N⁴-benzoyl-5'-O-mesyl-2,3'-anhydro-2'-deoxycytidine
  参考文献：
  名称：

  DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

  摘要：

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.010
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 吡啶 、 三甲基氯硅烷 作用下， 反应 5.0h， 生成 N⁴-benzoyl-3',5'-O-dimesyl-2'-deoxycytidine
  参考文献：
  名称：

  DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer

  摘要：

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.010

文献信息

• Study on Disulfur-Backboned Nucleic Acids: Part 3. Efficient Synthesis of 3′,5′-Dithio-2′-Deoxyuridine and Deoxycytidine
  作者：Peihua Shang、Hua Wang、Changmei Cheng、Hongchao Zheng、Yufen Zhao

  DOI：10.1080/15257770802520474

  日期：2008.11.13

  synthesizing 3',5'-dithio-2'-deoxypyrimidine nucleosides 6 and 13 from normal 2'-deoxynucleosides. 2,3'-Anhydronucleosides 2 and 9 are applied as intermediates in the process to reverse the conformation of 3'-position on sugar rings. The intramolecular rings of 2,3'-anhydrothymidine and uridine are opened by thioacetic acid directly to produce 3'-S-acetyl-3'-thio-2'-deoxynucleosides 3 or 5. To cytidine

  描述了用于从正常的2′-脱氧核苷合成3′，5′-二硫代2′-脱氧嘧啶核苷6和13的通用方法。2,3'-脱水核苷2和9在该过程中用作中间体，以逆转糖环上3'-位置的构象。2,3'-脱水胸苷和尿苷的分子内环通过硫代乙酸直接打开，以生成3'-S-乙酰基-3'-硫代-2'-脱氧核苷3或5。对于胞苷，OH（-）离子交换树脂用C 1开环，得到2′-脱氧胞苷10，其中3′-OH为苏糖构象。3'-OH被MsCl活化，然后被硫代乙酸钾取代，形成S，S'-二乙酰基3'，5'-二硫代2'-脱氧胞苷12。3'，5'中的乙酰基
• Pyrimidinnucleoside, ihre Herstellung und pharmazeutische Mittel
  申请人：MATTHES, Eckart, Dr.

  公开号：EP0409227A2

  公开（公告）日：1991-01-23

  Die Erfindung betrifft neue und bekannte Pyrimidin- und Purinnucleoside, die besonders wirksam gegen Hepatitis B-Infektionen sind und ihre Herstellung.

  本发明涉及对乙型肝炎感染特别有效的新的和已知的嘧啶和嘌呤核苷及其制备方法。
• US5053499A
  申请人：——

  公开号：US5053499A

  公开（公告）日：1991-10-01
• DNG cytidine: synthesis and binding properties of octameric guanidinium-linked deoxycytidine oligomer
  作者：Istvan E. Szabo、Thomas C. Bruice

  DOI：10.1016/j.bmc.2004.05.010

  日期：2004.8.1

  The synthesis of guanidinium-linked cytidyl oligomer (DNG-C-8), a cationic DNA analog, and the corresponding cytidine monomers is described. The DNG monomer synthesis was streamlined to produce a shorter route to the final monomer than previously reported for thymidine and subsequent solid-phase synthesis produced an octameric cytidyl DNG strand. Because octameric deoxyguanosine would be used as the complementary strand in our studies, it was necessary to investigate guanosine self-association. Singular value decomposition was used to mathematically deconvolve the spectral data and confirm the presence of transitions due to DNA-G(8) self-association. Job plots show the binding stoichiometry of DNG-C-8 with DNA-G(8) to be 1: 1. Thermal denaturation studies of the DNG-C-8-DNA-G(8) duplex established a T-m greater than or equal to 90degreesC and a DeltaGdegrees = 13.3 kcal mol(-1), indicating the DNG-C(8)(.)DNA-G(8) duplex is over 1000 times more stable than that of DNA-C(8)(.)DNA-G(8). (C) 2004 Elsevier Ltd. All rights reserved.