(2S,4R,5S,6R)-2-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-5-methoxy-4,6-dimethylheptan-3-one | 1187630-16-5

• 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,4R,5S,6R)-2-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-5-methoxy-4,6-dimethylheptan-3-one
• CAS: 1187630-16-5
• 化学式: C₂₃H₄₀O₄Si
• 分子量: 408.654
• InChiKey: KQVQNZYVIBFADI-GHDARCQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S,6R)-2-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-5-methoxy-4,6-dimethylheptan-3-one 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4S,5S,6R)-2-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methoxy-4,6-dimethylheptan-3-ol
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833
• 作为产物：
  描述：

  (2S,4R,5S,6R)-2-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-4,6-dimethylheptan-3-one 、 三氟甲烷磺酸甲酯 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到(2S,4R,5S,6R)-2-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-5-methoxy-4,6-dimethylheptan-3-one
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833