(4R,4aR,9aS)-4-((tert-butyldimethylsilyl)oxy)-9a-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydro-1H-xanthene-1,9(9aH)-dione | 1449752-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (4R,4aR,9aS)-4-((tert-butyldimethylsilyl)oxy)-9a-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydro-1H-xanthene-1,9(9aH)-dione
• CAS: 1449752-21-9
• 化学式: C₂₂H₃₂O₆Si
• 分子量: 420.578
• InChiKey: ZAUGNSPVTKBZES-YHYVQYDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,4aR,9aS)-4-((tert-butyldimethylsilyl)oxy)-9a-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydro-1H-xanthene-1,9(9aH)-dione 在 HF-pyridine 作用下， 以 四氢呋喃 为溶剂， 反应 60.0h， 以43%的产率得到
  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：

  (4R,4aS)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydroxanthen-9-one 在 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以32%的产率得到(4R,4aR,9aS)-4-((tert-butyldimethylsilyl)oxy)-9a-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydro-1H-xanthene-1,9(9aH)-dione
  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