(+)-(5S,7R,13R,2E,10E)-5-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid | 263369-10-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+)-(5S,7R,13R,2E,10E)-5-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid
• 英文别名: (E,5S,7R)-5-[Tert-butyl(diphenyl)silyl]oxy-7-[(E,5R)-5-hydroxyhex-2-enoyl]oxyoct-2-enoic acid
• CAS: 263369-10-4
• 化学式: C₃₀H₄₀O₆Si
• 分子量: 524.73
• InChiKey: XPHFJTUHJOPMKL-TUBGLDLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(5S,7R,13R,2E,10E)-5-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 57.0h， 生成 (+)-(6R,14R,12S,3E,9E)-6,14-dimethyl-12-(tert-butyldiphenylsilyloxy)-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione
  参考文献：
  名称：

  Enantioselective Synthesis of the Unsymmetrical Bis(lactone) (−)-(3E,6R,9E,12S,14R)-Colletol Induced by Chiral Sulfoxides and an Approach to (+)-Colletodiol by Asymmetric Hydroxylation of an α,β-Hydroxy Lactone

  摘要：

  A general synthetic strategy towards the two bis(lactones) (-)-colletol (1) and (+)-colletodiol (2) is described. A common intermediate in this synthesis is the 6-membered hydroxy lactone (+)-(3R,SR)-3-hydroxy-5-hexanolide (6), readily prepared by stereoselective reduction of (+)-(SR)-methyl 3,5-dioxo -6-(p-toluenesulfinyl)hexanoate (7). Stereoselective hydroxylation of this hydroxy lactone has allowed efficient access to (+)-colletodiol(2).

  DOI：

  10.1002/(sici)1099-0690(200001)2000:2<357::aid-ejoc357>3.0.co;2-n
• 作为产物：
  描述：

  3'-methyl-2'-butenyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate 在 4-二甲氨基吡啶 、 碘 作用下， 以 环己烷 、 甲苯 为溶剂， 反应 7.5h， 生成 (+)-(5S,7R,13R,2E,10E)-5-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of the Unsymmetrical Bis(lactone) (−)-(3E,6R,9E,12S,14R)-Colletol Induced by Chiral Sulfoxides and an Approach to (+)-Colletodiol by Asymmetric Hydroxylation of an α,β-Hydroxy Lactone

  摘要：

  A general synthetic strategy towards the two bis(lactones) (-)-colletol (1) and (+)-colletodiol (2) is described. A common intermediate in this synthesis is the 6-membered hydroxy lactone (+)-(3R,SR)-3-hydroxy-5-hexanolide (6), readily prepared by stereoselective reduction of (+)-(SR)-methyl 3,5-dioxo -6-(p-toluenesulfinyl)hexanoate (7). Stereoselective hydroxylation of this hydroxy lactone has allowed efficient access to (+)-colletodiol(2).

  DOI：

  10.1002/(sici)1099-0690(200001)2000:2<357::aid-ejoc357>3.0.co;2-n