3'-O-lauroyl ara-C | 53758-41-1

• 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'-O-lauroyl ara-C
• 英文别名: 4-amino-1-(O³-dodecanoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one；[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dodecanoate
• CAS: 53758-41-1
• 化学式: C₂₁H₃₅N₃O₆
• 分子量: 425.525
• InChiKey: YQYYWLUJJKVLGO-XWPNQZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  月桂酸乙烯酯 、 阿糖胞苷 在 Lipozyme IMRM 作用下， 生成 3'-O-lauroyl ara-C 、 5'-O-lauroyl ara-C
  参考文献：
  名称：

  Efficient synthesis of 5′-O-laurate of 1-β-d-arabinofuranosylcytosine via highly regioselective enzymatic acylation in binary solvent mixtures

  摘要：

  Regioselective enzymatic acylations of 1-beta-D-arabinofuranosylcytosine (ara-C) with vinyl laurate (VL) in binary organic solvents were explored for the preparation of 5'-O-laurate of ara-C. Among the nine kinds of enzymes, Novozym 435 showed the highest regioselectivity (>99.9%) towards the 5'-OH of ara-C. This lipase showed higher catalytic activity in hexane-pyridine than in other tested solvent mixtures. The most suitable VL to ara-C molar ratio, initial water activity, and reaction temperature were shown to be 15: 1, 0.07, and 50 degrees C, respectively, under which the initial reaction rate and the maximum substrate conversion were as high as 84.0 mmol L (1) h (1) and 98.1%, respectively. The product of Novozym 435-catalyzed acylation was characterized by C-13 NMR and con. rmed to be 5'-O-laurate of ara-C. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.077

文献信息

• Efficient synthesis of 5′-O-laurate of 1-β-d-arabinofuranosylcytosine via highly regioselective enzymatic acylation in binary solvent mixtures
  作者：Xiao-feng Li、Min-hua Zong、Guang-lei Zhao

  DOI：10.1016/j.bmcl.2010.05.077

  日期：2010.7

  Regioselective enzymatic acylations of 1-beta-D-arabinofuranosylcytosine (ara-C) with vinyl laurate (VL) in binary organic solvents were explored for the preparation of 5'-O-laurate of ara-C. Among the nine kinds of enzymes, Novozym 435 showed the highest regioselectivity (>99.9%) towards the 5'-OH of ara-C. This lipase showed higher catalytic activity in hexane-pyridine than in other tested solvent mixtures. The most suitable VL to ara-C molar ratio, initial water activity, and reaction temperature were shown to be 15: 1, 0.07, and 50 degrees C, respectively, under which the initial reaction rate and the maximum substrate conversion were as high as 84.0 mmol L (1) h (1) and 98.1%, respectively. The product of Novozym 435-catalyzed acylation was characterized by C-13 NMR and con. rmed to be 5'-O-laurate of ara-C. (C) 2010 Elsevier Ltd. All rights reserved.