<2-(2)H>-(2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene | 154976-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <2-(2)H>-(2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene
• 英文别名: (1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-deuterio-1-[(4R,5S)-2,2-dimethyl-5-(2-methylprop-1-enyl)-1,3-dioxolan-4-yl]ethanol
• CAS: 154976-40-6
• 化学式: C₁₇H₃₄O₄Si
• 分子量: 331.532
• InChiKey: RINHJOBWPBOMEJ-CAQUYFEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <2-(2)H>-(2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene 在 二甲基硫 、 臭氧 作用下， 生成 <4-(2)H>-5-O-<(1,1-Dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-α-D-ribofuranose 、 <4-(2)H>-5-O-<(1,1-Dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-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
• 作为产物：
  描述：

  (2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene 在 硼氘化钠 、 重水 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 <2-(2)H>-(2R,3S,4S)-1-O-<(1,1-Dimethylethyl)dimethylsilyl>-2-hydroxy-6-methyl-3,4-O-(1-methylethylidene)hept-5-ene
  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

文献信息

• General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides
  作者：James J. De Voss、Jon J. Hangeland、Craig A. Townsend

  DOI：10.1021/jo00089a013

  日期：1994.5

  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.