1-(5'-O-benzoyl-α-D-arabinofuranosyl)thymine | 1039628-51-7

• 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: 1-(5'-O-benzoyl-α-D-arabinofuranosyl)thymine
• 英文别名: [(2R,3S,4S,5S)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 1039628-51-7
• 化学式: C₁₇H₁₈N₂O₇
• 分子量: 362.339
• InChiKey: MBXHULDEJNNQLN-CXTNEJHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲酸乙烯酯 、 1-(α-D-arabinofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 在 Candida antarctica lipase B 作用下， 以 乙腈 为溶剂， 反应 144.0h， 以64%的产率得到1-(5'-O-benzoyl-α-D-arabinofuranosyl)thymine
  参考文献：
  名称：

  Efficient and Selective Enzymatic Acylation Reaction: Separation of Furanosyl and Pyranosyl Nucleosides

  摘要：

  Candida antarctica lipase-B (CAL-B) immobilized on lewatite selectively acylated the primary hydroxyl group of the furanosyl nucleoside in a mixture of 1-(alpha-D-arabinofuranosyl)thymine and 1-(alpha-D-arabinopyranosyl)thymine. This selective biocatalytic acylation of furanosyl nucleoside has enabled us an easy separation of arabinofuranosyl thymine from an inseparable mixture with arabinopyranosyl thymine. The primary hydroxyl selective acylation methodology of arabinonucleoside has also been successfully used for the separation of 1-(beta-D-xylofuranosyl)thymine and 1-(beta-D-xylopyranosyl)thymine from a mixture of the two, which demonstrate the generality of the enzymatic methodology for separation of furanosyl and pyranosyl nucleosides.

  DOI：

  10.1021/jo800731u

文献信息

• Efficient and Selective Enzymatic Acylation Reaction: Separation of Furanosyl and Pyranosyl Nucleosides
  作者：Jyotirmoy Maity、Gaurav Shakya、Sunil K. Singh、Vasulinga T. Ravikumar、Virinder S. Parmar、Ashok K. Prasad

  DOI：10.1021/jo800731u

  日期：2008.7.1

  Candida antarctica lipase-B (CAL-B) immobilized on lewatite selectively acylated the primary hydroxyl group of the furanosyl nucleoside in a mixture of 1-(alpha-D-arabinofuranosyl)thymine and 1-(alpha-D-arabinopyranosyl)thymine. This selective biocatalytic acylation of furanosyl nucleoside has enabled us an easy separation of arabinofuranosyl thymine from an inseparable mixture with arabinopyranosyl thymine. The primary hydroxyl selective acylation methodology of arabinonucleoside has also been successfully used for the separation of 1-(beta-D-xylofuranosyl)thymine and 1-(beta-D-xylopyranosyl)thymine from a mixture of the two, which demonstrate the generality of the enzymatic methodology for separation of furanosyl and pyranosyl nucleosides.