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 | 885683-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 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
• CAS: 885683-83-0
• 化学式: C₄₂H₇₂O₆Si₂
• 分子量: 729.201
• InChiKey: RRNAHHHPVPWIKC-HCIRKMNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.85
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 正丁基锂 、 2,4,6-三氯苯甲酰氯 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 99.11h， 生成 (1R,7S,9E,11S,17R)-7-[(E,1S)-1-hydroxy-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]prop-2-enyl]-11-(methoxymethoxy)-13-methylidene-6,21-dioxabicyclo[15.3.1]henicosa-9,19-dien-3-yn-5-one
  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：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以81%的产率得到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