methyl (S)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethyl-4-oxochroman-2-yl)butanoate | 1449752-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl (S)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethyl-4-oxochroman-2-yl)butanoate
• CAS: 1449752-19-5
• 化学式: C₂₃H₃₆O₆Si
• 分子量: 436.621
• InChiKey: RDEVITYOQGAFJE-CVDCTZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethyl-4-oxochroman-2-yl)butanoate 在 titanium(IV) isopropylate 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以69%的产率得到(4S,4aS)-(tert-dimethylsilyl)oxy-1-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydroxanthen-9-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Diversonol

  摘要：

  AbstractFor the synthesis of (−)‐diversonol (ent‐1), an enantioselective domino‐Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96 % and 93 % ee, respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig–Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent‐1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac‐1,9 a‐epi‐diversonol (rac‐41) is also described.

  DOI：

  10.1002/chem.201204037
• 作为产物：
  描述：

  在 叔丁基过氧化氢 、 palladium 10% on activated carbon 、 氢气 作用下， 以 癸烷 、 乙酸乙酯 为溶剂， 反应 96.5h， 生成 methyl (S)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethyl-4-oxochroman-2-yl)butanoate
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Diversonol

  摘要：

  AbstractFor the synthesis of (−)‐diversonol (ent‐1), an enantioselective domino‐Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96 % and 93 % ee, respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig–Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent‐1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac‐1,9 a‐epi‐diversonol (rac‐41) is also described.

  DOI：

  10.1002/chem.201204037