5'-O-octanoylthymidine | 124169-74-0

• 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: 5'-O-octanoylthymidine
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl octanoate
• CAS: 124169-74-0
• 化学式: C₁₈H₂₈N₂O₆
• 分子量: 368.43
• InChiKey: KCCGQVFFLDYUCK-RRFJBIMHSA-N

物化性质

• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  O-octanoyl acetoxime 、 beta-胸苷 以 四氢呋喃 为溶剂， 反应 20.0h， 以72%的产率得到5'-O-octanoylthymidine
  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

• Acyl deoxyribonucleoside derivatives and uses thereof
  申请人：PRO-NEURON, INC.

  公开号：EP0712629A1

  公开（公告）日：1996-05-22

  Use of acyl derivatives of deoxyribonucleosides in manufacture of a medicament for enhancing haematopoesis or enhancing healing of bone marrow.

  使用脱氧核苷酸的酰基衍生物制造增强造血或促进骨髓愈合的药物。
• ACYL DEOXYRIBONUCLEOSIDE DERIVATIVES AND USES THEREOF
  申请人：PRO-NEURON, INC.

  公开号：EP0355131B1

  公开（公告）日：1996-09-04
• US6297222B1
  申请人：——

  公开号：US6297222B1

  公开（公告）日：2001-10-02
• US6348451B1
  申请人：——

  公开号：US6348451B1

  公开（公告）日：2002-02-19
• US6306834B1
  申请人：——

  公开号：US6306834B1

  公开（公告）日：2001-10-23