(E,2S,3S,4S,6R)-9-((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-3-hydroxy-7-O-(tert-butyldimethylsilyl)-2,4,6-trimethylnon-8-enyl acetate | 947380-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,2S,3S,4S,6R)-9-((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-3-hydroxy-7-O-(tert-butyldimethylsilyl)-2,4,6-trimethylnon-8-enyl acetate
• 英文别名: [(E,2S,3S,4S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl]-7-hydroxy-2,4,6-trimethylnon-8-enyl] acetate
• CAS: 947380-91-8
• 化学式: C₂₈H₅₄O₆Si
• 分子量: 514.819
• InChiKey: HIKGEKKPJPUICQ-SXGHNCJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,2S,3S,4S,6R)-9-((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-3-hydroxy-7-O-(tert-butyldimethylsilyl)-2,4,6-trimethylnon-8-enyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(E,2S,3S,4S,6R)-9-((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-3-O-(tert-butyldimethylsilyl)-2,4,6-trimethylnon-8-ene-1,7-diol
  参考文献：
  名称：

  Stereoselective Formal Total Synthesis of (+)-Methynolide

  摘要：

  A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo0704762
• 作为产物：
  描述：

  ((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)methanol 在 chromium dichloride 、 偶氮二异丁腈 、 三正丁基氢锡 、 戴斯-马丁氧化剂 、 三苯基膦 、 nickel dichloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.0h， 生成 (E,2S,3S,4S,6R)-9-((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)-3-hydroxy-7-O-(tert-butyldimethylsilyl)-2,4,6-trimethylnon-8-enyl acetate
  参考文献：
  名称：

  Stereoselective Formal Total Synthesis of (+)-Methynolide

  摘要：

  A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.

  DOI：

  10.1021/jo0704762