N-benzoyl-β-L-2'-deoxycytidine | 189074-86-0

• 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: N-benzoyl-β-L-2'-deoxycytidine
• 英文别名: N-[1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 189074-86-0
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: MPSJHJFNKMUKCN-DYEKYZERSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzoyl-β-L-2'-deoxycytidine 以71的产率得到[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  2’,3’－双脱氧胞苷的合成方法

  摘要：

  本发明涉及2’，3’－双脱氧胞苷(I)的合成方法。该方法以2’－脱氧胞苷盐酸盐为起始原料经脱盐处理、选择性氨基和羟基保护、选择性脱氧脱保护、催化氢化脱保护等反应制得目的产物。与现有的合成方法相比，该法反应步骤短，收率高，所得产物纯度高。

  公开号：

  CN1640883A
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 以83的产率得到N-benzoyl-β-L-2'-deoxycytidine
  参考文献：
  名称：

  2’,3’－双脱氧胞苷的合成方法

  摘要：

  本发明涉及2’，3’－双脱氧胞苷(I)的合成方法。该方法以2’－脱氧胞苷盐酸盐为起始原料经脱盐处理、选择性氨基和羟基保护、选择性脱氧脱保护、催化氢化脱保护等反应制得目的产物。与现有的合成方法相比，该法反应步骤短，收率高，所得产物纯度高。

  公开号：

  CN1640883A

文献信息

• Enzymatic Parallel Kinetic Resolution of Mixtures of <scp>d</scp>/<scp>l</scp> 2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-<scp>l</scp>-Nucleosides
  作者：Saúl Martínez-Montero、Susana Fernández、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1021/jo101368z

  日期：2010.10.1

  We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of beta-D/L-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with beta-D- and beta-L-nucleosides furnished acylated compounds that have different R-f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of beta-D- and beta-L-2'-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3'-O-levulination of the beta-D enantiomer, whereas the 5'-OH group was acylated in 2'-deoxy-beta-L-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSL's substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of beta-D/L-nucleosides.
• Regioselective Enzymatic Acylation of β-<scp>l</scp>-2‘-Deoxynucleosides:  Application in Resolution of β-<scp>d</scp>/<scp>l</scp>-2‘-Deoxynucleosides
  作者：Javier García、Susana Fernández、Miguel Ferrero、Yogesh S. Sanghvi、Vicente Gotor

  DOI：10.1021/ol048502v

  日期：2004.10.1

  (GRAPHICS)A practical synthesis Of beta-L-3'- and beta-L-5'-O-levulinyl-2'-deoxynucleosides has been described for the first time through enzymatic acylation and/or hydrolysis processes. It is noteworthy that the different behavior exhibited by Pseudomonas cepacia lipase in the acylation of D- and L-nucleosides allows the parallel kinetic resolution Of D/L-nucleosides.
• [EN] METHOD OF SEQUENCING L-POLYNUCLEOTIDE<br/>[FR] PROCÉDÉ DE SÉQUENÇAGE DE L-POLYNUCLÉOTIDE
  申请人：[en]DXOME INC.

  公开号：WO2023183345A2

  公开（公告）日：2023-09-28

  The present disclosure provides a novel method of amplifying and sequencing L-form polynucleotide. Further provided include L-form nucleotides and D-form enzymes that can be used in the method. The method of making the L-form nucleotides and D-form enzymes are also provided.
• 2’,3’－双脱氧胞苷的合成方法
  申请人：杭州富邦生物制药有限公司

  公开号：CN1640883A

  公开（公告）日：2005-07-20

  本发明涉及2’，3’－双脱氧胞苷(I)的合成方法。该方法以2’－脱氧胞苷盐酸盐为起始原料经脱盐处理、选择性氨基和羟基保护、选择性脱氧脱保护、催化氢化脱保护等反应制得目的产物。与现有的合成方法相比，该法反应步骤短，收率高，所得产物纯度高。