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 | 911834-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• 英文别名: 4-[(2R,6R)-2-[(2S,6S,7E,10S,11S)-10,11-dihydroxy-6-(methoxymethoxy)-2-methyl-4-methylidenetrideca-7,12-dienyl]-3,6-dihydro-2H-pyran-6-yl]but-2-ynoic acid
• CAS: 911834-87-2
• 化学式: C₂₆H₃₈O₇
• 分子量: 462.584
• InChiKey: XSBDQVREHQEZJQ-SAKDTNPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 Lindlar's catalyst 喹啉 、 ruthenium carbene complex 、 1-己烯 、 二甲基溴化硼 、 2,4,6-三氯苯甲酰氯 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 32.03h， 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：

  (Z)-(5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-octa-3,7-dienal 在 正丁基锂 、 D-tartaric acid derivative 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 82.79h， 生成 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
  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

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。
• 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.