2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl diacetate | 382141-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl diacetate
• 英文别名: [3-Acetyloxy-2-[(5-methyl-2,4-dioxopyrimidin-1-yl)methoxy]propyl] acetate
• CAS: 382141-09-5
• 化学式: C₁₃H₁₈N₂O₇
• 分子量: 314.295
• InChiKey: SWWCXWFGYWKCIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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 diacetate 生成 1-<<2-hydroxy-1-(hydroxymethyl)ethoxy>methyl>thymine
  参考文献：
  名称：

  OGAWA, TAKASHI;TAKAKU, HIROSHI;YAMAMOTO, NAOKI, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 499-504

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(1,3-dichloropropan-2-yloxymethyl)-5-methylpyrimidine-2,4-dione 、 potassium acetate 生成 2-((5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)propane-1,3-diyl diacetate
  参考文献：
  名称：

  OGAWA, TAKASHI;TAKAKU, HIROSHI;YAMAMOTO, NAOKI, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 499-504

  摘要：

  DOI：

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。
• Enantioselective enzymatic desymmetrization of the prochiral pyrimidine acyclonucleoside
  作者：Renata Kołodziejska、Marcin Górecki、Jadwiga Frelek、Marcin Dramiński

  DOI：10.1016/j.tetasy.2012.05.003

  日期：2012.5

  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.