(2R,3R,5R)-5-bromomethyl-2-methyltetrahydrofuran-3-ol | 632330-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,5R)-5-bromomethyl-2-methyltetrahydrofuran-3-ol
• 英文别名: (2R,3R,5R)-5-(bromomethyl)-2-methyloxolan-3-ol
• CAS: 632330-51-9
• 化学式: C₆H₁₁BrO₂
• 分子量: 195.056
• InChiKey: XJHXWTMEEOPHDG-HSUXUTPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (2R,3R,5R)-5-bromomethyl-2-methyltetrahydrofuran-3-ol 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2R,3R,5R)-5-bromomethyl-2-methyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

  摘要：

  A new synthesis of (-)-muscarine, (+)-allo-muscarine, (-)-epi-muscarine, and (-)-epiallo-muscarine has been devised which utilizes selective alkoxyl radical cyclizations for constructing tri-substituted tetrahydrofuran units. Photolysis of (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazole-2(3H)thione in the presence of BrCCl3 provided (2R,3S,5S)-3-benzoyloxy-5-broniomethyl-2-methyltetrahydrofuran as the major product and the corresponding (2R,3S,5R)-isomer as the minor. These building blocks were converted into enantiomerically pure (+)-allo-muscarine (from the major alkoxyl radical cyclization product) and (-)-muscarine (from the minor product). Temperature and substituent effects on the diastereoselectivity of the underlying alkoxyl radical cyclization have been investigated. (-)-epi-Muscarine and (-)-epiallo-muscarine have been prepared likewise, starting from (2R.3R)-ev-(3-benzoyloxy-5-hexen-2-oxy)-4-metliylthiazole-2(3H)thione. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.06.006
• 作为产物：
  描述：

  (2S,3R)-3-benzoyloxy-5-hexen-2-ol 在 三乙烯二胺 、 sodium hydroxide 、 三氯溴甲烷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 121.42h， 生成 (2R,3R,5R)-5-bromomethyl-2-methyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis of enantiopure (2R)-configured muscarine alkaloids via selective alkoxyl radical ring-closure reactions

  摘要：

  A new synthesis of (-)-muscarine, (+)-allo-muscarine, (-)-epi-muscarine, and (-)-epiallo-muscarine has been devised which utilizes selective alkoxyl radical cyclizations for constructing tri-substituted tetrahydrofuran units. Photolysis of (2R,3S)-N-(3-benzoyloxy-5-hexen-2-oxy)-4-methylthiazole-2(3H)thione in the presence of BrCCl3 provided (2R,3S,5S)-3-benzoyloxy-5-broniomethyl-2-methyltetrahydrofuran as the major product and the corresponding (2R,3S,5R)-isomer as the minor. These building blocks were converted into enantiomerically pure (+)-allo-muscarine (from the major alkoxyl radical cyclization product) and (-)-muscarine (from the minor product). Temperature and substituent effects on the diastereoselectivity of the underlying alkoxyl radical cyclization have been investigated. (-)-epi-Muscarine and (-)-epiallo-muscarine have been prepared likewise, starting from (2R.3R)-ev-(3-benzoyloxy-5-hexen-2-oxy)-4-metliylthiazole-2(3H)thione. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.06.006