tert-butyl [(2R,3R,4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] carbonate | 1227248-63-6

• 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: tert-butyl [(2R,3R,4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] carbonate
• CAS: 1227248-63-6
• 化学式: C₂₀H₃₄N₂O₈Si
• 分子量: 458.584
• InChiKey: PYOISBSYDYFUCS-DTZQCDIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2R,3R,4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] carbonate 以 2,2,2-三氟乙醇 为溶剂， 反应 1.0h， 以97%的产率得到5'-O-(tert-butyldimethylsilyl)uridine
  参考文献：
  名称：

  A novel practical cleavage of tert-butyl esters and carbonates using fluorinated alcohols

  摘要：

  Thermolytic cleavage of t-butyl esters and t-butyl carbonates was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvent. Thus, a practical method to cleanly convert t-butyl esters and carbonates into the corresponding carboxylic acids, decarboxylated products, or alcohols in nearly quantitative yields was developed. The product is recovered by a simple solvent evaporation. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic esters. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.100

文献信息

• A novel practical cleavage of tert-butyl esters and carbonates using fluorinated alcohols
  作者：Jason Choy、Saul Jaime-Figueroa、Teresa Lara-Jaime

  DOI：10.1016/j.tetlet.2010.02.100

  日期：2010.4

  Thermolytic cleavage of t-butyl esters and t-butyl carbonates was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvent. Thus, a practical method to cleanly convert t-butyl esters and carbonates into the corresponding carboxylic acids, decarboxylated products, or alcohols in nearly quantitative yields was developed. The product is recovered by a simple solvent evaporation. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic esters. (C) 2010 Elsevier Ltd. All rights reserved.