(E)-(2R,3S,4S)-1-((2R,3R)-3-Hydroxymethyl-oxiranyl)-3-methyl-hept-5-ene-2,4-diol | 321995-02-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(2R,3S,4S)-1-((2R,3R)-3-Hydroxymethyl-oxiranyl)-3-methyl-hept-5-ene-2,4-diol
• 英文别名: (E,2R,3S,4S)-1-[(2R,3R)-3-(hydroxymethyl)oxiran-2-yl]-3-methylhept-5-ene-2,4-diol
• CAS: 321995-02-2
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: CDQIQMCJJZXSHH-XRNUIYAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3S,4S)-1-((2R,3R)-3-Hydroxymethyl-oxiranyl)-3-methyl-hept-5-ene-2,4-diol 在 2,6-二甲基吡啶 、 amberlyst-15 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 [(2S,3R,4R,6S)-6-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-3-methyl-2-[(E)-prop-1-enyl]oxan-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g
• 作为产物：
  描述：

  (2E,8E)-(5R,6S,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-deca-2,8-dienoic acid methyl ester 在 四丁基氟化铵 、 二异丁基氢化铝 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (E)-(2R,3S,4S)-1-((2R,3R)-3-Hydroxymethyl-oxiranyl)-3-methyl-hept-5-ene-2,4-diol
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g

文献信息

• Total Synthesis of (+)-Ratjadone
  作者：Mathias Christmann、Ulhas Bhatt、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1002/1521-3773(20001201)39:23<4364::aid-anie4364>3.0.co;2-g

  日期：2000.12.1
• The First Total Synthesis of (+)-Ratjadone
  作者：Ulhas Bhatt、Mathias Christmann、Monika Quitschalle、Eckhard Claus、Markus Kalesse

  DOI：10.1021/jo005768g

  日期：2001.3.1

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.