(2R,2'R)- and (2R,2'S)-(E)-5-methyl-2-(((tetrahydropyran-2-yl)oxy)methyl)-1-((p-toluenesulfonyl)oxy)hex-3-ene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,2'R)- and (2R,2'S)-(E)-5-methyl-2-(((tetrahydropyran-2-yl)oxy)methyl)-1-((p-toluenesulfonyl)oxy)hex-3-ene
• 英文别名: (2R,2'R)- and (2R,2'S)-(E)-5-methyl-2-{[(tetrahydropyran-2-yl)oxy]methyl}-1-[(p-toluenesulfonyl)oxy]hex-3-ene；[(E,2R)-5-methyl-2-(oxan-2-yloxymethyl)hex-3-enyl] 4-methylbenzenesulfonate
• 化学式: C₂₀H₃₀O₅S
• 分子量: 382.521
• InChiKey: HONFTUPFYCHTEE-ZWZYXGOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,2'R)- and (2R,2'S)-(E)-5-methyl-2-(((tetrahydropyran-2-yl)oxy)methyl)-1-((p-toluenesulfonyl)oxy)hex-3-ene 在 sodium tetrahydroborate 、 二甲基硫 、 臭氧 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Methanesulfonic acid (S)-2-(tetrahydro-pyran-2-yloxymethyl)-butyl ester
  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：

  (R)-(E)-2-(acetoxymethyl)-5-methyl-1-((p-toluenesulfonyl)oxy)hex-3-ene 在 lithium hydroxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (2R,2'R)- and (2R,2'S)-(E)-5-methyl-2-(((tetrahydropyran-2-yl)oxy)methyl)-1-((p-toluenesulfonyl)oxy)hex-3-ene
  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

• Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methane
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano、M. Teresa Zannetti

  DOI：10.1021/jo00058a036

  日期：1993.3

  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.