Butyric acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester | 145355-70-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Butyric acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl butanoate
• CAS: 145355-70-0
• 化学式: C₁₄H₁₈N₄O₆
• 分子量: 338.32
• InChiKey: PUXNHGUXKZUATQ-FRJWGUMJSA-N

物化性质

• 沸点：
  711.0±60.0 °C(predicted)
• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Acetoneoxime butyrate 、 肌苷 以 四氢呋喃 为溶剂， 反应 24.0h， 以86%的产率得到Butyric acid (2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction

  摘要：

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.

  DOI：

  10.1021/jo00055a018

文献信息

• Manipulation of enzyme regioselectivity by solvent engineering: Enzymatic synthesis of 5′-O-acylribonucleosides
  作者：Haribansh K. Singh、Gregory L. Cote、Trina M. Hadfield

  DOI：10.1016/s0040-4039(00)76216-2

  日期：1994.2

  Regioselectivity of enzyme can be manipulated by solvent engineering. By this technique, a simple and convenient method was developed for the synthesis of 5′-O-acylribonucleosides in high yields by the protease-catalyzed regioselective esterification of the primary hydroxyl groups of ribonucleosides in anhydrous pyridine.

  酶的区域选择性可以通过溶剂工程来控制。通过这种技术，开发了一种简单方便的方法，用于通过无水吡啶中核糖核苷的伯羟基的蛋白酶催化的区域选择性酯化来高产率地合成5'-O-酰基核糖核苷。