(2R,2'R)- and (2R,2'S)-2-((tetrahydropyran-2-yloxy)methyl)-1-butanol | 172587-07-4

• 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: (2R,2'R)- and (2R,2'S)-2-((tetrahydropyran-2-yloxy)methyl)-1-butanol
• 英文别名: (2R)-2-(oxan-2-yloxymethyl)butan-1-ol
• CAS: 172587-07-4
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: KIIHPKLHSBQLTB-YHMJZVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,2'R)- and (2R,2'S)-2-((tetrahydropyran-2-yloxy)methyl)-1-butanol 在 盐酸 、 四丁基碘化铵 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 (R)-3-Hydroxymethyl-pentanenitrile
  参考文献：
  名称：

  Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane

  摘要：

  Asymmetrized tria(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported. Preparation of bottom half fragment 3 was achieved through a ''protecting group-controlled'' stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.

  DOI：

  10.1021/jo00058a036
• 作为产物：
  描述：

  (2R,2'R)- and (2R,2'S)-(E)-2-((2-ethyl-5-methylhex-3-enyl)oxy)tetrahydropyran 在 sodium tetrahydroborate 、 二甲基硫 、 臭氧 作用下， 生成 (2R,2'R)- and (2R,2'S)-2-((tetrahydropyran-2-yloxy)methyl)-1-butanol
  参考文献：
  名称：

  Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane

  摘要：

  Asymmetrized tria(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported. Preparation of bottom half fragment 3 was achieved through a ''protecting group-controlled'' stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.

  DOI：

  10.1021/jo00058a036

文献信息

• Guanti, Giuseppe; Banfi, Luca; Zannetti, Maria Teresa, Gazzetta Chimica Italiana, 1995, vol. 125, # 8, p. 333 - 340
  作者：Guanti, Giuseppe、Banfi, Luca、Zannetti, Maria Teresa

  DOI：——

  日期：——