(1R,7S,9E,11S,15S,17R)-7-[(1S)-1-hydroxyprop-2-enyl]-11-(methoxymethoxy)-15-methyl-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one | 911834-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1R,7S,9E,11S,15S,17R)-7-[(1S)-1-hydroxyprop-2-enyl]-11-(methoxymethoxy)-15-methyl-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one
• CAS: 911834-80-5
• 化学式: C₂₆H₃₆O₆
• 分子量: 444.568
• InChiKey: BRKYVKLMAKTMSY-SAKDTNPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,7S,9E,11S,15S,17R)-7-[(1S)-1-hydroxyprop-2-enyl]-11-(methoxymethoxy)-15-methyl-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one 在 Lindlar's catalyst 喹啉 、 ruthenium carbene complex 、 1-己烯 、 二甲基溴化硼 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 30.5h， 生成 (3Z,9E)-(1R,7S,11S,15S,17R)-7-((E)-(S)-3-Cyclohexyl-1-hydroxy-allyl)-11-hydroxy-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one
  参考文献：
  名称：

  Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy

  摘要：

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.

  DOI：

  10.1021/ol061619u
• 作为产物：
  描述：

  4-[(2R,6R)-6-((E)-(2S,6S,10S,11S)-10,11-Dihydroxy-6-methoxymethoxy-2-methyl-4-methylene-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-ynoic acid 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 、 水 、 碳酸氢钠 作用下， 以 苯 为溶剂， 反应 3.53h， 以43%的产率得到(1R,7S,9E,11S,15S,17R)-7-[(1S)-1-hydroxyprop-2-enyl]-11-(methoxymethoxy)-15-methyl-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one
  参考文献：
  名称：

  LAULIMALIDE AND LAULIMALIDE ANALOGS

  摘要：

  描述了新型laulimalide类似物、治疗增殖性疾病的方法以及合成laulimalide和新型laulimalide类似物的过程。

  公开号：

  US20080227851A1

文献信息

• LAULIMALIDE AND LAULIMALIDE ANALOGS
  申请人：WENDER PAUL A.

  公开号：US20080227851A1

  公开（公告）日：2008-09-18

  Novel laulimalide analogs, methods for the treatment of proliferative disease and processes for the synthesis of laulimalide and novel laulimalide analogs are described.

  描述了新型laulimalide类似物、治疗增殖性疾病的方法以及合成laulimalide和新型laulimalide类似物的过程。
• NOVEL LAULIMALIDE ANALOGUES AS THERAPEUTIC AGENTS
  申请人：WENDER PAUL A.

  公开号：US20090099252A1

  公开（公告）日：2009-04-16

  Laulimalide analogues useful as microtubule stabilizing agents, and in the treatment of abnormal cell proliferation, are disclosed. Methods of making the compounds, as well as methods of using such compounds in treating abnormal cell proliferation diseases are also described.
• Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy
  作者：Paul A. Wender、Michael K. Hilinski、Philip R. Skaanderup、Nicolas G. Soldermann、Susan L. Mooberry

  DOI：10.1021/ol061619u

  日期：2006.8.1

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.