(3R,5S)-5-(hydroxymethyl)tetrahydrofuran-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (3R,5S)-5-(hydroxymethyl)tetrahydrofuran-3-ol
• 英文别名: (3R,5S)-5-(hydroxymethyl)oxolan-3-ol
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: WDMXOLOBWMBITN-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)tetrahydrofuran-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(3R,5S)-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols

  摘要：

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.047

文献信息

• Intramolecular addition of carbon radicals to aldehydes: synthesis of enantiopure tetrahydrofuran-3-ols
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2007.04.047

  日期：2007.6

  A simple and efficient substrate-controlled asymmetric synthesis of enantiopure tetrahydrofuran-3-ols by a 5-exo-trig radical cyclization is described. This cyclization occurs when a delta-carbon radical adds intramolecularly to the carbonyl group of an aldehyde. The delta-carbon radicals can be efficiently produced from the tin hydride mediated deselenenylation of 5-phenylseleno-3-oxapentanals, which were easily prepared starting from commercially available enantiopure epoxides or chlorohydrins. (c) 2007 Elsevier Ltd. All rights reserved.