(2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-2-(2-methylene-6-trimethylsilanyloxy-hexyl)-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane | 900518-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-2-(2-methylene-6-trimethylsilanyloxy-hexyl)-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane
• 英文别名: [(4R,6R,8R,10S,13R)-4-(1,3-dithian-2-ylmethyl)-13-methyl-10-(2-methylidene-6-trimethylsilyloxyhexyl)-5,7,9-trioxadispiro[5.1.58.26]pentadecan-13-yl]oxy-triethylsilane
• CAS: 900518-83-4
• 化学式: C₃₄H₆₄O₅S₂Si₂
• 分子量: 673.182
• InChiKey: DAGXYWCUCMXYSQ-VUBIVAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.27
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-2-(2-methylene-6-trimethylsilanyloxy-hexyl)-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane 在 叔丁基锂 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 8.33h， 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：

  1,7,9-Trioxadispiro[5.1.5.2]pentadecane-2-acetaldehyde,10-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-5-methyl-5-[(triethylsilyl)oxy]-, (2S,5R,6R,8R,10R)- 在 吡啶 、 咪唑 、 六甲基磷酰三胺 、 正丁基锂 、 草酰氯 、 碘 、 叔丁基锂 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 、 正戊烷 、 苯 为溶剂， 反应 12.25h， 生成 (2S,5R,6R,8R,10R)-10-[1,3]Dithian-2-ylmethyl-5-methyl-2-(2-methylene-6-trimethylsilanyloxy-hexyl)-5-triethylsilanyloxy-1,7,9-trioxa-dispiro[5.1.5.2]pentadecane
  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

文献信息

• Unified Total Synthesis of Pteriatoxins and Their Diastereomers
  作者：Fumiyoshi Matsuura、René Peters、Masahiro Anada、Scott S. Harried、Junliang Hao、Yoshito Kishi

  DOI：10.1021/ja0618954

  日期：2006.6.1

  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.