(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate | 850835-63-1

• 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: (E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate
• 英文别名: [(E,3R,5S)-5-hydroxy-8-methoxy-3-methyl-8-oxooct-6-enyl] 2,4,6-trimethylbenzoate
• CAS: 850835-63-1
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: MVYGJSSYUQAYEH-IRVACUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate 在 咪唑 、 4-二甲氨基吡啶 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.17h， 生成 (E)-(4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-oct-2-enedial
  参考文献：
  名称：

  Total Synthesis of Brasoside and Littoralisone

  摘要：

  The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

  DOI：

  10.1021/ja050064f
• 作为产物：
  描述：

  (S)-5-formyl-3-methylpentyl 2,4,6-trimethylbenzoate 、 膦酰基乙酸甲酯二乙酯 在 亚硝基苯 、 D-脯氨酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 氯化铵 作用下， 以 二甲基亚砜 、 乙腈 、 甲醇 为溶剂， 反应 48.75h， 以56%的产率得到(E,3R,5S)-7-(methoxycarbonyl)-5-hydroxy-3-methylhept-6-enyl 2,4,6-trimethylbenzoate
  参考文献：
  名称：

  Total Synthesis of Brasoside and Littoralisone

  摘要：

  The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

  DOI：

  10.1021/ja050064f

文献信息

• Total Synthesis of Brasoside and Littoralisone
  作者：Ian K. Mangion、David W. C. MacMillan

  DOI：10.1021/ja050064f

  日期：2005.3.1

  The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed alpha-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.