(5S,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-5,6-dihydro-pyran-2-one | 870075-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5S,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-5,6-dihydro-pyran-2-one
• CAS: 870075-13-1
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: WBPKEQLSJXIGPG-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5S,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-5,6-dihydro-pyran-2-one 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以93%的产率得到(5S,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m
• 作为产物：
  描述：

  (3S,4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-3-methyl-hept-1-en-4-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (5S,6R)-6-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-5-methyl-5,6-dihydro-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m