5-((2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-ylmethyl)-hex-5-en-1-ol | 900519-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-((2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-ylmethyl)-hex-5-en-1-ol
• CAS: 900519-40-6
• 化学式: C₃₁H₅₆O₅S₂Si
• 分子量: 601.0
• InChiKey: IWKLLVATGXCWLB-QOWCOUPESA-N

物化性质

• 沸点：
  655.2±55.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  39.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-((2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-ylmethyl)-hex-5-en-1-ol 在 吡啶 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 正戊烷 为溶剂， 反应 8.83h， 生成
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954
• 作为产物：
  描述：

  {(2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-2-[6-(4-methoxy-benzyloxy)-2-methylene-hexyl]-5-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-5-yloxy}-triethyl-silane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以93%的产率得到5-((2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-2-ylmethyl)-hex-5-en-1-ol
  参考文献：
  名称：

  Unified Total Synthesis of Pteriatoxins and Their Diastereomers

  摘要：

  A unified total synthesis is reported to access all of the possible diastereomers of pteriatoxins A-C, with the use of an intramolecular Diels-Alder reaction as the key step to form the carbo-macrocyclic core structure. The C34/C35-diol protecting groups were found to have significant effects on both the exo/endo-selectivity and the exo-facial selectivity of the intramolecular Diels-Alder process.

  DOI：

  10.1021/ja0618954