(2S,3S)-3-[(4-methoxyphenyl)methoxy]hept-6-ene-1,2-diol | 158673-92-8

• 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: (2S,3S)-3-[(4-methoxyphenyl)methoxy]hept-6-ene-1,2-diol
• CAS: 158673-92-8
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: SIKYRUNIKDWJQJ-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-[(4-methoxyphenyl)methoxy]hept-6-ene-1,2-diol 在 吡啶 、 2,6-二甲基吡啶 、 sodium hydroxide 、 硼烷四氢呋喃络合物 、 二甲基硫 、 苯基溴化硒 、 四丁基氟化铵 、 双氧水 、 potassium carbonate 、 臭氧 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 64.84h， 生成 全内酯
  参考文献：
  名称：

  An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate

  摘要：

  An enantioselective total synthesis of the cis-fused tetrahydrofurano-2-pyrone (+)-altholactone (1) from diethyl L-tartrate via the L-threitol derivative 2 is described. The remaining two stereogenic centers of 1 are introduced by a highly stereoselective hydroboration-oxidation sequence.

  DOI：

  10.1016/s0040-4020(01)89432-1
• 作为产物：
  描述：

  ethyl (4R,5S)-5-but-3-enyl-2-(4-methoxyphenyl)-1,3-dioxolane-4-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 120.25h， 以92%的产率得到(2S,3S)-3-[(4-methoxyphenyl)methoxy]hept-6-ene-1,2-diol
  参考文献：
  名称：

  Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and syn-Selective Vinylogous Aldol Chemistry

  摘要：

  An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent Innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently In the synthesis of the C1-C15 and C16-C25 subunits, respectively.

  DOI：

  10.1021/ol400014e

文献信息

• Formal Synthesis of Palmerolide A, Featuring Alkynogenic Fragmentation and <i>syn</i>-Selective Vinylogous Aldol Chemistry
  作者：Marilda P. Lisboa、David M. Jones、Gregory B. Dudley

  DOI：10.1021/ol400014e

  日期：2013.2.15

  An enantioselective route to palmerolide A is described. The approach features original syntheses of three subunits, which are then assembled to produce a known late-stage intermediate and formally provide the highest overall yield of the natural product reported to date. Recent Innovations in alkynogenic fragmentation and vinylogous aldol methodology figure prominently In the synthesis of the C1-C15 and C16-C25 subunits, respectively.
• An enantioselective total synthesis of (+)-altholactone from diethyl L-tartrate
  作者：Peter Somfai

  DOI：10.1016/s0040-4020(01)89432-1

  日期：1994.1

  An enantioselective total synthesis of the cis-fused tetrahydrofurano-2-pyrone (+)-altholactone (1) from diethyl L-tartrate via the L-threitol derivative 2 is described. The remaining two stereogenic centers of 1 are introduced by a highly stereoselective hydroboration-oxidation sequence.