3',5'-di-O-levulinoyl-β-L-thymidine | 793716-98-0

• 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: 3',5'-di-O-levulinoyl-β-L-thymidine
• 英文别名: levulinoyl(-3)[levulinoyl(-5)]2-deoxy-L-eryPenf(b)-thymin-1-yl；[(2S,3R,5S)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-(4-oxopentanoyloxy)oxolan-2-yl]methyl 4-oxopentanoate
• CAS: 793716-98-0
• 化学式: C₂₀H₂₆N₂O₉
• 分子量: 438.434
• InChiKey: WVXZZDFJASUPPB-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-levulinoyl-β-L-thymidine 在 Candida antarctica lipase B 、 phosphate buffer 、 immobilized Pseudomonas cepacia lipase 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 38.5h， 生成 5'-O-levulinoyl-β-L-thymidine
  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 、 替比夫定 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 1.0h， 以95%的产率得到3',5'-di-O-levulinoyl-β-L-thymidine
  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.