(3S,4S,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)(3,4-dimethoxyphenyl)methyl)-4-(3,4-dimethoxyphenyl)-3-hydroxydihydrofuran-2(3H)-one | 1537880-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3S,4S,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)(3,4-dimethoxyphenyl)methyl)-4-(3,4-dimethoxyphenyl)-3-hydroxydihydrofuran-2(3H)-one
• CAS: 1537880-83-3
• 化学式: C₂₇H₃₈O₈Si
• 分子量: 518.679
• InChiKey: WXIONWCHYCVLHL-QORCZRPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)(3,4-dimethoxyphenyl)methyl)-4-(3,4-dimethoxyphenyl)-3-hydroxydihydrofuran-2(3H)-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以1.41 g的产率得到(2S,3S,4S,5S)-5-((tert-butyldimethylsilyl)oxy)-3,5-bis(3,4-dimethoxyphenyl)pentane-1,2,4-triol
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055
• 作为产物：
  描述：

  (4R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)(3,4-dimethoxyphenyl)methyl)-4-(3,4-dimethoxyphenyl)dihydrofuran-2(3H)-one 在 oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3S,4S,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)(3,4-dimethoxyphenyl)methyl)-4-(3,4-dimethoxyphenyl)-3-hydroxydihydrofuran-2(3H)-one
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055