methyl (R)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethylchroman-2-yl)butanoate | 1449752-11-7

• 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 (R)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethylchroman-2-yl)butanoate
• 英文别名: methyl (4R)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(2S)-5-methoxy-2,7-dimethyl-3,4-dihydrochromen-2-yl]butanoate
• CAS: 1449752-11-7
• 化学式: C₂₃H₃₈O₅Si
• 分子量: 422.637
• InChiKey: XUAYYXHDFRQUOL-OFNKIYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethylchroman-2-yl)butanoate 在 titanium(IV) isopropylate 、 tris-(dipivaloylmethanato)manganese(III) 、 苯硅烷 、 氧气 、 四氯化钛 、 三乙胺 、 HF-pyridine 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 苯 为溶剂， 反应 291.0h， 生成 (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：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 以1.15 g的产率得到methyl (R)-4-(tert-butyldimethylsilyloxy)-4-((S)-5-methoxy-2,7-dimethylchroman-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