(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(1S,2S,3S,4R)-2-hydroxy-4-(4-methoxybenzyloxy)-1,3-dimethylpentyl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione | 236401-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(1S,2S,3S,4R)-2-hydroxy-4-(4-methoxybenzyloxy)-1,3-dimethylpentyl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
• 英文别名: (3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3S,4S,5R)-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
• CAS: 236401-66-4
• 化学式: C₄₆H₆₄O₁₀
• 分子量: 777.008
• InChiKey: CIKXHZIQLRJCLA-WMPRZOQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(1S,2S,3S,4R)-2-hydroxy-4-(4-methoxybenzyloxy)-1,3-dimethylpentyl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione 在 吡啶 、 咪唑 、 水 、 戴斯-马丁氧化剂 、 氟化氢吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 elaiolide
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c
• 作为产物：
  描述：

  (1E,3S,4S,5R,6S,7S,8R)-1-iodo-8-(4-methoxybenzyloxy)-3,5,7-trimethylnon-1-en-4,6-diol 、 (E)-3-碘-2-丙酸 以356 mg的产率得到(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(1S,2S,3S,4R)-2-hydroxy-4-(4-methoxybenzyloxy)-1,3-dimethylpentyl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
  参考文献：
  名称：

  Total Synthesis of Elaiolide Using a Copper(I)-Promoted Stille Cyclodimerization Reaction

  摘要：

  The 16-membered macrodiolide elaiolide (2) has been prepared in 20 steps from the ketone (S)-8 in 9.3% overall yield with a diastereoselectivity of 76%, Key steps included the copper(I) thiophene-2-carboxylate promoted cyclodimerization of the vinyl stannane 3 to give the C-2-symmetric macrocycle 16 in 80% yield and the two directional aldol coupling of the macrocyclic diketone 17 with aldehyde 5. Most of the stereocenters in the macrocyclic precursor 3 were constructed using boron aldol methodology developed in this laboratory.

  DOI：

  10.1021/ol990004c