3',5'-di-O-levulinoyl-β-L-2'-deoxycytidine

• 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: 3',5'-di-O-levulinoyl-β-L-2'-deoxycytidine
• 英文别名: [(2S,3R,5S)-5-(4-amino-2-oxopyrimidin-1-yl)-3-(4-oxopentanoyloxy)oxolan-2-yl]methyl 4-oxopentanoate
• 化学式: C₁₉H₂₅N₃O₈
• 分子量: 423.423
• InChiKey: OXLIPTTUMNYMJM-YCPHGPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-levulinoyl-β-L-2'-deoxycytidine 在 Candida antarctica lipase B 、 phosphate buffer 作用下， 以 1,4-二氧六环 为溶剂， 反应 127.0h， 以89%的产率得到3'-O-levulinoyl-β-L-2'-deoxycytidine
  参考文献：
  名称：

  Regioselective Enzymatic Acylation of β-l-2‘-Deoxynucleosides:  Application in Resolution of β-d/l-2‘-Deoxynucleosides

  摘要：

  (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.

  DOI：

  10.1021/ol048502v
• 作为产物：
  描述：

  乙酰丙酸 、 4-氨基-1-(2-脱氧-beta-L-赤式-呋喃戊糖基)-2(1H)-嘧啶酮 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以75%的产率得到3',5'-di-O-levulinoyl-β-L-2'-deoxycytidine
  参考文献：
  名称：

  Regioselective Enzymatic Acylation of β-l-2‘-Deoxynucleosides:  Application in Resolution of β-d/l-2‘-Deoxynucleosides

  摘要：

  (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.

  DOI：

  10.1021/ol048502v

文献信息

• 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.