2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl dibutyrate | 1384553-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl dibutyrate
• 英文别名: [3-Butanoyloxy-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]propyl] butanoate
• CAS: 1384553-56-3
• 化学式: C₁₇H₂₆N₂O₇
• 分子量: 370.403
• InChiKey: YJAPARZFEACKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl dibutyrate 在 Burkholderia cepacia Amano PS lipase 、 水 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 生成 3-hydroxy-2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propyl butyrate
  参考文献：
  名称：

  Enantioselective enzymatic desymmetrization of the prochiral pyrimidine acyclonucleoside

  摘要：

  The effect of the solvent and the acyl group donor on the selectivity of the transesterification reaction of {[(1,3-dihydroxypropan-2-yl)oxy]methyl}-5-methylpyrimidine-2.4(1H,3H)-dione was examined. Lipase (EC 3.1.1.3) Amano PS from Burkholderia cepacia (BCL) enabled desymmetrization of prochiral hydroxyl groups and gave the (R)-monoester in high enantiomeric excess (ee 88-99%). The best selectivity was obtained for the transesterification reaction with vinyl benzoate as the acylating agent (only monoester, 99% ee). The absolute configuration of the newly formed stereogenic center was determined with a high degree of confidence on the basis of the combined experimental and theoretical electronic circular dichroic (ECD) studies. The hydrolysis of prochiral diesters formed during the transesterification reaction in the presence of BCL provided the opposite enantiomer, that is, the (S)-monoester. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.003
• 作为产物：
  描述：

  正丁酸乙烯酯 、 1-<<2-hydroxy-1-(hydroxymethyl)ethoxy>methyl>thymine 在 Burkholderia cepacia Amano PS lipase 作用下， 以 甲基叔丁基醚 为溶剂， 反应 24.0h， 以63.5%的产率得到3-hydroxy-2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propyl butyrate
  参考文献：
  名称：

  Enantioselective enzymatic desymmetrization of the prochiral pyrimidine acyclonucleoside

  摘要：

  The effect of the solvent and the acyl group donor on the selectivity of the transesterification reaction of {[(1,3-dihydroxypropan-2-yl)oxy]methyl}-5-methylpyrimidine-2.4(1H,3H)-dione was examined. Lipase (EC 3.1.1.3) Amano PS from Burkholderia cepacia (BCL) enabled desymmetrization of prochiral hydroxyl groups and gave the (R)-monoester in high enantiomeric excess (ee 88-99%). The best selectivity was obtained for the transesterification reaction with vinyl benzoate as the acylating agent (only monoester, 99% ee). The absolute configuration of the newly formed stereogenic center was determined with a high degree of confidence on the basis of the combined experimental and theoretical electronic circular dichroic (ECD) studies. The hydrolysis of prochiral diesters formed during the transesterification reaction in the presence of BCL provided the opposite enantiomer, that is, the (S)-monoester. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.003

文献信息

• <i>Candida antarctica</i>lipase B catalyzed enantioselective acylation of pyrimidine acyclonucleoside
  作者：Renata Kołodziejska、Aleksandra Karczmarska-Wódzka、Andrzej Wolan、Marcin Dramiński

  DOI：10.3109/10242422.2012.715637

  日期：2012.8

  Abstract The influence of solvent and acyl group donor on selectivity of the transesterification reaction of 1-[1′,3′-dihydroxy-2′-propoxymethyl]-5-methyluracil, a structural analogue of ganciclovir was examined. Lipase (EC 3.1.1.3) B from Candida antarctica (CALB) enabled desymmetrization of prochiral hydroxyl groups when 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim][PF6]) was used as a

  摘要 研究了溶剂和酰基供体对更昔洛韦结构类似物1-[1',3'-二羟基-2'-丙氧基甲基]-5-甲基尿嘧啶酯交换反应选择性的影响。当 1-丁基-3-甲基咪唑鎓六氟磷酸盐 ([Bmim][PF6]) 用作反应介质时，来自南极念珠菌 (CALB) 的脂肪酶 (EC 3.1.1.3) B 能够使前手性羟基去对称化。据观察，CALB 在离子液体 [Bmim][PF6] 中的对映选择性是传统有机溶剂的 2.7-4 倍。