(-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate | 566203-39-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate
• 英文别名: [(2S)-4-[(2S,3R)-3-[(4-methoxyphenyl)methoxy]pent-4-en-2-yl]oxy-4-oxobutan-2-yl] (E,4R,5S)-4-(2-methoxyethoxymethoxy)-5-prop-2-enoyloxyhex-2-enoate
• CAS: 566203-39-2
• 化学式: C₃₀H₄₂O₁₁
• 分子量: 578.657
• InChiKey: SWTMTFYOWHKPGS-LDRFQASNSA-N

物化性质

• 沸点：
  625.4±55.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate 在 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 (-)-1-[3-(methoxy)methoxy-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate
  参考文献：
  名称：

  Total Synthesis of Macrosphelides A, B, and E:  First Application of Ring-Closing Metathesis for Macrosphelide Synthesis

  摘要：

  A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.

  DOI：

  10.1021/jo035435u
• 作为产物：
  描述：

  (3R,4S)-4-(tert-butyldimethylsilyloxy)pent-1-en-3-ol 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 170.0h， 生成 (-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate
  参考文献：
  名称：

  Total Synthesis of Macrosphelides A, B, and E:  First Application of Ring-Closing Metathesis for Macrosphelide Synthesis

  摘要：

  A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.

  DOI：

  10.1021/jo035435u

文献信息

• New Strategy for the Total Synthesis of Macrosphelides A and B Based on Ring-Closing Metathesis
  作者：Yuji Matsuya、Takanori Kawaguchi、Hideo Nemoto

  DOI：10.1021/ol0350689

  日期：2003.8.1

  [reaction: see text] A new total synthesis of macrosphelides A and B using ring-closing metathesis (RCM) as a macrocyclization step is described. The substrate of the RCM could be synthesized from readily available chiral materials, methyl (S)-(+)-3-hydroxybutyrate and methyl (S)-(-)-lactate, with a high efficiency. The RCM proceeded in the presence of Grubbs' Ru-complex, providing a new effective synthetic

  [反应：见正文]描述了使用闭环复分解（RCM）作为大环化步骤的新的大环内酯A和B的全合成。RCM的底物可以由容易获得的手性材料，（S）-（+）-3-羟基丁酸甲酯和（S）-（-）-乳酸甲酯合成。RCM在Grubbs的Ru-络合物存在下进行，为这些天然产物提供了一条新的有效合成途径。
• Total Synthesis of Macrosphelides A, B, and E:  First Application of Ring-Closing Metathesis for Macrosphelide Synthesis
  作者：Takanori Kawaguchi、Nobutaka Funamori、Yuji Matsuya、Hideo Nemoto

  DOI：10.1021/jo035435u

  日期：2004.1.1

  A new synthetic route for macrosphelides A, B, and E based on ring-closing metathesis (RCM) was established. The substrates for RCM could be synthesized starting from commercially available chiral materials, methyl (S)-lactate and methyl (S)- or (R)-3-hydroxybutyrate, in good overall yields. In the investigation of the key RCM step, it was found that the steric factor around the reaction site significantly affected the reaction rate of macrocyclization. A detailed account regarding this synthetic study is described herein.