(2S,3R,5S)-2-(tert-butyldimethylsilanyloxymethyl)-5-methoxytetrahydrofuran-3-carbaldehyde | 1448549-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,3R,5S)-2-(tert-butyldimethylsilanyloxymethyl)-5-methoxytetrahydrofuran-3-carbaldehyde
• CAS: 1448549-96-9
• 化学式: C₁₃H₂₆O₄Si
• 分子量: 274.433
• InChiKey: WHTNQPLIGRJIHO-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S)-2-(tert-butyldimethylsilanyloxymethyl)-5-methoxytetrahydrofuran-3-carbaldehyde 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.17h， 生成 2-amino-8-((2S,3S,5S)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-yl)-9H-purin-6-ol
  参考文献：
  名称：

  Molybdopterin Biosynthesis: Trapping an Unusual Purine Ribose Adduct in the MoaA-Catalyzed Reaction

  摘要：

  MoaA/MoaC catalyze a remarkable rearrangement reaction in which guanosine-5'-triphosphate (GTP) is converted to cyclic pyranopterin monophosphate (cPMP). In this reaction, the C8 of GTP is inserted between the C2' and the C3' carbons of the GTP ribose. Previous experiments with GTP isotopomers demonstrated that the ribose C3' hydrogen atom is abstracted by the adenosyl radical. This led to a novel mechanistic proposal involving an intermediate with a bond between the C8 of guanine and C3' of the ribose. This paper describes the use of 2',3'-dideoxyGTP to trap this intermediate.

  DOI：

  10.1021/ja4041048
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 三苯基膦 、 1,1,3,3-四甲基脲 、 lithium bromide 作用下， 以 甲苯 、 苯 为溶剂， 反应 9.5h， 生成 (2S,3R,5S)-2-(tert-butyldimethylsilanyloxymethyl)-5-methoxytetrahydrofuran-3-carbaldehyde
  参考文献：
  名称：

  Molybdopterin Biosynthesis: Trapping an Unusual Purine Ribose Adduct in the MoaA-Catalyzed Reaction

  摘要：

  MoaA/MoaC catalyze a remarkable rearrangement reaction in which guanosine-5'-triphosphate (GTP) is converted to cyclic pyranopterin monophosphate (cPMP). In this reaction, the C8 of GTP is inserted between the C2' and the C3' carbons of the GTP ribose. Previous experiments with GTP isotopomers demonstrated that the ribose C3' hydrogen atom is abstracted by the adenosyl radical. This led to a novel mechanistic proposal involving an intermediate with a bond between the C8 of guanine and C3' of the ribose. This paper describes the use of 2',3'-dideoxyGTP to trap this intermediate.

  DOI：

  10.1021/ja4041048