5-methyl-1-[(2R,4S,5R)-4-triethylsilyloxy-5-(triethylsilyloxymethyl)oxolan-2-yl]-3-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione | 1237843-32-1

• 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: 5-methyl-1-[(2R,4S,5R)-4-triethylsilyloxy-5-(triethylsilyloxymethyl)oxolan-2-yl]-3-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione
• CAS: 1237843-32-1
• 化学式: C₂₈H₅₆N₂O₆Si₃
• 分子量: 601.019
• InChiKey: GSQFTUZRDLUILB-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.33
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-methyl-1-[(2R,4S,5R)-4-triethylsilyloxy-5-(triethylsilyloxymethyl)oxolan-2-yl]-3-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione 在 甲醇 、 甲酸 作用下， 以76%的产率得到N3-(2-(trimethylsilyl)ethoxy)methyl-thymidine
  参考文献：
  名称：

  Chemoselective Deprotection of Triethylsilyl Ethers

  摘要：

  An efficient and selective method was developed for the deprotection of triethylsilyl (TES) ethers using formic acid in methanol (5-10%) or in methylene chloride 2-5%) with excellent yields. TES ethers are selectively deprotected to the corresponding alcohols in high yields using formic acid in methanol under mild reaction conditions. Other hydroxyl protecting groups like t-butyldimethylsilyl (TBDMS) remain unaffected.

  DOI：

  10.1080/15257770903362172

文献信息

• Chemoselective Deprotection of Triethylsilyl Ethers
  作者：Tilak Chandra、William E. Broderick、Joan B. Broderick

  DOI：10.1080/15257770903362172

  日期：2009.12.7

  An efficient and selective method was developed for the deprotection of triethylsilyl (TES) ethers using formic acid in methanol (5-10%) or in methylene chloride 2-5%) with excellent yields. TES ethers are selectively deprotected to the corresponding alcohols in high yields using formic acid in methanol under mild reaction conditions. Other hydroxyl protecting groups like t-butyldimethylsilyl (TBDMS) remain unaffected.