O-((6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[4,5-f][1,3,5,2,4]trioxadisilocin-9-yl-8-13C) O-phenyl carbonothioate | 144963-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-((6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[4,5-f][1,3,5,2,4]trioxadisilocin-9-yl-8-13C) O-phenyl carbonothioate
• CAS: 144963-52-0
• 化学式: C₃₅H₄₇N₃O₈SSi₂
• 分子量: 726.999
• InChiKey: BOTLCOFFRZUOPJ-COLICASCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  119.37
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  O-((6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[4,5-f][1,3,5,2,4]trioxadisilocin-9-yl-8-13C) O-phenyl carbonothioate 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 N-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl-2-13C)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
  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：

  Phenylsulfenyl <1-(13)C>-2,3,5-tri-O-benzoyl-β-D-ribofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.08h， 生成 O-((6aR,8R,9R,9aR)-8-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2,4,4-tetraisopropyltetrahydro-6H-furo[4,5-f][1,3,5,2,4]trioxadisilocin-9-yl-8-13C) O-phenyl carbonothioate
  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