3'-methyl-2'-butenyl (+)-(5S,7R,13R,2E,10E)-13-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoate | 263369-09-1

• 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: 3'-methyl-2'-butenyl (+)-(5S,7R,13R,2E,10E)-13-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoate
• 英文别名: 3-methylbut-2-enyl (E,5S,7R)-7-[(E,5R)-5-[tert-butyl(dimethyl)silyl]oxyhex-2-enoyl]oxy-5-[tert-butyl(diphenyl)silyl]oxyoct-2-enoate
• CAS: 263369-09-1
• 化学式: C₄₁H₆₂O₆Si₂
• 分子量: 707.111
• InChiKey: NTFVJSWHPSZKSB-BHQLOYSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  49
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-methyl-2'-butenyl (+)-(5S,7R,13R,2E,10E)-13-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoate 在 碘 、 4-甲基苯磺酸吡啶 作用下， 以 环己烷 、 乙醇 为溶剂， 反应 54.0h， 以71%的产率得到(+)-(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
• 作为产物：
  描述：

  (R)-3-(tert-butyldimethylsilyloxy)-1-butanol 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 44.5h， 生成 3'-methyl-2'-butenyl (+)-(5S,7R,13R,2E,10E)-13-(tert-butyldimethylsilyloxy)-5-(tert-butyldiphenylsilyloxy)-7-methyl-9-oxo-8-oxatetradeca-2,10-dienoate
  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

文献信息

• 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
  作者：Guy Solladié、Laurence Gressot、Françoise Colobert

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

  日期：2000.1

  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).