(4R,4aS)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydroxanthen-9-one | 1449752-14-0

• 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: (4R,4aS)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydroxanthen-9-one
• CAS: 1449752-14-0
• 化学式: C₂₂H₃₂O₅Si
• 分子量: 404.579
• InChiKey: IPEKJRKMEMUHQP-VGOFRKELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,4aS)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4a-tetrahydroxanthen-9-one 在 HF-pyridine 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 192.0h， 以72%的产率得到(4R,4aS)-1,4-dihydroxy-8-methoxy-4a,6-dimethyl-2,3,4,4atetrahydroxanthen-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：

  methyl (R)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethyl-chroman-2-yl)butanoate 在 titanium(IV) isopropylate 、 tris-(dipivaloylmethanato)manganese(III) 、 苯硅烷 、 氧气 、 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 97.0h， 生成 (4R,4aS)-4-(tert-butyldimethylsilyloxy)-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