(2S,4S,5S)-methyl 6-((2S,6S)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate | 1236147-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4S,5S)-methyl 6-((2S,6S)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate
• 英文别名: methyl (2S,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(2S,6S)-4,4-dimethoxy-6-(phenylmethoxymethyl)oxan-2-yl]-2,4-dimethylhexanoate
• CAS: 1236147-06-0
• 化学式: C₃₀H₅₂O₇Si
• 分子量: 552.824
• InChiKey: UYWSOCYWBCKAFJ-CVSNDOPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-methyl 6-((2S,6S)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 7.0h， 以94%的产率得到(2S,4S,5S)-methyl 5-(tert-butyldimethylsilyloxy)-6-((2S,6S)-6-(hydroxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-2,4-dimethylhexanoate
  参考文献：
  名称：

  Total Synthesis of Enigmazole A from Cinachyrella enigmatica. Bidirectional Bond Constructions with an Ambident 2,4-Disubstituted Oxazole Synthon

  摘要：

  The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.

  DOI：

  10.1021/ja1016975
• 作为产物：
  描述：

  、 原甲酸三甲酯 在 camphorsulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2S,4S,5S)-methyl 6-((2R,6S)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate 、 (2S,4S,5S)-methyl 6-((2S,6R)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate 、 (2S,4S,5S)-methyl 6-((2S,6S)-6-(benzyloxymethyl)-4,4-dimethoxytetrahydro-2H-pyran-2-yl)-5-(tertbutyldimethylsilyloxy)-2,4-dimethylhexanoate
  参考文献：
  名称：

  Total Synthesis of Enigmazole A from Cinachyrella enigmatica. Bidirectional Bond Constructions with an Ambident 2,4-Disubstituted Oxazole Synthon

  摘要：

  The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.

  DOI：

  10.1021/ja1016975