(2R,6R)-2-(4-Trimethylsilanylmethyl-pent-4-enyl)-6-(3-trimethylsilanyl-prop-2-ynyl)-3,6-dihydro-2H-pyran | 885683-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,6R)-2-(4-Trimethylsilanylmethyl-pent-4-enyl)-6-(3-trimethylsilanyl-prop-2-ynyl)-3,6-dihydro-2H-pyran
• 英文别名: trimethyl-[2-methylidene-5-[(2R,6R)-6-(3-trimethylsilylprop-2-ynyl)-3,6-dihydro-2H-pyran-2-yl]pentyl]silane
• CAS: 885683-73-8
• 化学式: C₂₀H₃₆OSi₂
• 分子量: 348.676
• InChiKey: CIGKDURYUYLIBH-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2-(4-Trimethylsilanylmethyl-pent-4-enyl)-6-(3-trimethylsilanyl-prop-2-ynyl)-3,6-dihydro-2H-pyran 在 Yamamoto's (acyloxy)borane 、 potassium carbonate 、 N,N-二异丙基乙胺 、 丙腈 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 87.0h， 生成 tert-butyl-[(1E,3S,4S,6E,8S)-3-[tert-butyl(dimethyl)silyl]oxy-8-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-10-methylidene-13-[(2R,6R)-6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl]trideca-1,6-dien-4-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of 11-Desmethyllaulimalide, a Highly Potent Simplified Laulimalide Analogue

  摘要：

  A step-economical synthesis of 11-desmethyllaulimalide (2) is reported. This simplified analogue is available through an improved second-generation synthetic approach to the laulimalides, in a shorter step count and from much less expensive starting material than the parent compound. This new lead retains the anticancer function of laulimalide.

  DOI：

  10.1021/ol060233g
• 作为产物：
  描述：

  1-(三甲基硅基)丙炔 在 四(三苯基膦)钯 正丁基锂 、 cerium(III) chloride 、 四甲基乙二胺 、 三正丁基氢锡 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 42.0h， 生成 (2R,6R)-2-(4-Trimethylsilanylmethyl-pent-4-enyl)-6-(3-trimethylsilanyl-prop-2-ynyl)-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of 11-Desmethyllaulimalide, a Highly Potent Simplified Laulimalide Analogue

  摘要：

  A step-economical synthesis of 11-desmethyllaulimalide (2) is reported. This simplified analogue is available through an improved second-generation synthetic approach to the laulimalides, in a shorter step count and from much less expensive starting material than the parent compound. This new lead retains the anticancer function of laulimalide.

  DOI：

  10.1021/ol060233g

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。
• Total Synthesis and Biological Evaluation of 11-Desmethyllaulimalide, a Highly Potent Simplified Laulimalide Analogue
  作者：Paul A. Wender、Michael K. Hilinski、Nicolas Soldermann、Susan L. Mooberry

  DOI：10.1021/ol060233g

  日期：2006.3.1

  A step-economical synthesis of 11-desmethyllaulimalide (2) is reported. This simplified analogue is available through an improved second-generation synthetic approach to the laulimalides, in a shorter step count and from much less expensive starting material than the parent compound. This new lead retains the anticancer function of laulimalide.