<4-(2)H>-1-O-Acetyl-5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-D-ribofuranose | 154976-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <4-(2)H>-1-O-Acetyl-5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-D-ribofuranose
• 英文别名: [(3aR,4R,6aR)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-deuterio-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl] acetate
• CAS: 154976-42-8
• 化学式: C₁₆H₃₀O₆Si
• 分子量: 347.488
• InChiKey: MFUROHCCMWEUBA-FFTQANNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <4-(2)H>-1-O-Acetyl-5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-D-ribofuranose 在 三氟乙酸 作用下， 反应 0.83h， 生成 <4'-(2)H>-N⁴-Benzoylcytidine
  参考文献：
  名称：

  General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides

  摘要：

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.

  DOI：

  10.1021/jo00089a013
• 作为产物：
  描述：

  乙酸酐 、 <4-(2)H>-5-O-<(1,1-Dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-D-ribofuranose 在 吡啶 作用下， 反应 4.0h， 以99%的产率得到<4-(2)H>-1-O-Acetyl-5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-D-ribofuranose
  参考文献：
  名称：

  General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides

  摘要：

  Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in [5'-H-2(2)]-, [4'-H-2]-, [1'-H-2]-, (5'R)-[5'-H-2]-, and (5'S)-[5'-H-2]-N-4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides. These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.

  DOI：

  10.1021/jo00089a013