(1R,5S,7S,9S,11R,13S)-7-methoxy-13-(methoxymethoxy)-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecan-3-one | 1017238-16-2

• 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: (1R,5S,7S,9S,11R,13S)-7-methoxy-13-(methoxymethoxy)-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecan-3-one
• CAS: 1017238-16-2
• 化学式: C₂₀H₃₆O₆
• 分子量: 372.502
• InChiKey: VUFGVBZOTMIQPQ-XREYTECCSA-N

物化性质

• 沸点：
  485.1±45.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,5S,7S,9S,11R,13S)-7-methoxy-13-(methoxymethoxy)-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecan-3-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.5h， 以97%的产率得到(1R,5S,7S,9S,11R,13S)-13-hydroxy-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecan-3-one
  参考文献：
  名称：

  Formal Total Synthesis of Neopeltolide

  摘要：

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.

  DOI：

  10.1021/ol8001255
• 作为产物：
  描述：

  在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 以83%的产率得到(1R,5S,7S,9S,11R,13S)-7-methoxy-13-(methoxymethoxy)-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecan-3-one
  参考文献：
  名称：

  Formal Total Synthesis of Neopeltolide

  摘要：

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.

  DOI：

  10.1021/ol8001255

文献信息

• Formal Total Synthesis of Neopeltolide
  作者：Viktor V. Vintonyak、Martin E. Maier

  DOI：10.1021/ol8001255

  日期：2008.3.1

  A concise synthesis of the core structure of the macrolide neopeltolide was developed featuring a Prins cyclization to fashion the pyran ring. Key steps in the synthesis of aldehyde 16 were a Leighton allylation and a Feringa-Minnaard asymmetric methyl cuprate addition to an unsaturated thioester. For lactonization, a classical Yamaguchi macrolactonization was used. The longest linear sequence consists of 17 steps providing lactone 26 with an overall yield of 23%.