Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside | 144963-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5S)-5-(benzenesulfinyl)-3,4-dibenzoyloxy(513C)oxolan-2-yl]methyl benzoate
• CAS: 144963-47-3；144963-68-8
• 化学式: C₃₂H₂₆O₈S
• 分子量: 571.609
• InChiKey: GXZQCGYOTLRDRL-RHSXMLQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 为溶剂， 反应 0.6h， 生成 N6-苯甲酰基腺苷
  参考文献：
  名称：

  PhenylsulfenylD-ribofuranosides as efficient ribosyl donors: Application to the synthesis of [1′,-13C]-(deoxy)nucleosides

  摘要：

  Readily available phenylsulfenyl 2,3,5-tri-O-benzoyl-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast, high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. The method has been applied to the synthesis of [1'-C-13] labelled nucleosides further transformed to building blocks ready for oligodeoxynucleotide construction.

  DOI：

  10.1016/s0040-4039(00)79089-7
• 作为产物：
  描述：

  Acetyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside 在 三氟化硼乙醚 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside
  参考文献：
  名称：

  PhenylsulfenylD-ribofuranosides as efficient ribosyl donors: Application to the synthesis of [1′,-13C]-(deoxy)nucleosides

  摘要：

  Readily available phenylsulfenyl 2,3,5-tri-O-benzoyl-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast, high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. The method has been applied to the synthesis of [1'-C-13] labelled nucleosides further transformed to building blocks ready for oligodeoxynucleotide construction.

  DOI：

  10.1016/s0040-4039(00)79089-7

文献信息

• PhenylsulfenylD-ribofuranosides as efficient ribosyl donors: Application to the synthesis of [1′,-13C]-(deoxy)nucleosides
  作者：Luc Chanteloup、Jean-Marie Beau

  DOI：10.1016/s0040-4039(00)79089-7

  日期：1992.9

  Readily available phenylsulfenyl 2,3,5-tri-O-benzoyl-beta-D-ribofuranoside glycosylates silylated nucleobases in a fast, high-yielding and stereoselective reaction promoted by trimethylsilyl trifluoromethanesulfonate. The method has been applied to the synthesis of [1'-C-13] labelled nucleosides further transformed to building blocks ready for oligodeoxynucleotide construction.