(R)-2-(tert-butyldimethylsilyloxy)-2-((S)-5-methoxy-2,7-dimethylchroman-2-yl)ethanol | 1449752-09-3

• 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: (R)-2-(tert-butyldimethylsilyloxy)-2-((S)-5-methoxy-2,7-dimethylchroman-2-yl)ethanol
• 英文别名: (2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(2S)-5-methoxy-2,7-dimethyl-3,4-dihydrochromen-2-yl]ethanol
• CAS: 1449752-09-3
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: KWCSYZKMIHIEEO-QUCCMNQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(tert-butyldimethylsilyloxy)-2-((S)-5-methoxy-2,7-dimethylchroman-2-yl)ethanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(S)-2-(tert-butyldimethylsilyloxy)-2-((S)-5-methoxy-2,7-dimethylchroman-2-yl)acetaldehyde
  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：

  4-(2,6-dimethoxy-4-methyl-phenyl)-butan-2-one 在 2,6-二甲基吡啶 、 正丁基锂 、 palladium(II) trifluoroacetate 、 甲基磺酰胺 、 C₄₀H₃₂N₂O₂ 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 HF-pyridine 、 对苯醌 、 乙硫醇钠 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 228.0h， 生成 (R)-2-(tert-butyldimethylsilyloxy)-2-((S)-5-methoxy-2,7-dimethylchroman-2-yl)ethanol
  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

文献信息

• Enantioselective Total Synthesis of (−)-Diversonol
  作者：Lutz F. Tietze、Stefan Jackenkroll、Christian Raith、Dirk A. Spiegl、Johannes R. Reiner、Maria Claudia Ochoa Campos

  DOI：10.1002/chem.201204037

  日期：2013.4.8

  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.