phenacyl 5'-thymidine carbonate | 252979-74-1

• 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: phenacyl 5'-thymidine carbonate
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl phenacyl carbonate
• CAS: 252979-74-1
• 化学式: C₁₉H₂₀N₂O₈
• 分子量: 404.376
• InChiKey: ZSKIBSGCDPFCKG-NUEKZKHPSA-N

物化性质

• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenacyl 5'-thymidine carbonate 在 9,10-二甲基蒽 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以91%的产率得到beta-胸苷
  参考文献：
  名称：

  Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof

  摘要：

  酒精、磷酸酯和二酸衍生物可能通过辐射去保护，所使用的保护基是芳基酰基或杂环芳基酰基。

  公开号：

  US06392089B1
• 作为产物：
  描述：

  2-羟基苯乙酮 以 硝基甲烷 为溶剂， 反应 3.0h， 生成 phenacyl 5'-thymidine carbonate
  参考文献：
  名称：

  Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids

  摘要：

  The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10-dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by-products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00754-1

文献信息

• Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids
  作者：Anamitro Banerjee、Kwangjoo Lee、Daniel E. Falvey

  DOI：10.1016/s0040-4020(99)00754-1

  日期：1999.10

  The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10-dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by-products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Photoreleasable protecting groups on alcohols, phosphates and diacids and the use thereof
  申请人：University of Maryland

  公开号：US06392089B1

  公开（公告）日：2002-05-21

  Alcohol, phosphate, and diacid derivatives that may be deprotected by irradiation are disclosed. The protecting group is an arylacyl or heteroarylacyl group.

  酒精、磷酸酯和二酸衍生物可能通过辐射去保护，所使用的保护基是芳基酰基或杂环芳基酰基。