methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate | 263369-07-9

• 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: methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate
• 英文别名: methyl (E,5S,7R)-5-[tert-butyl(diphenyl)silyl]oxy-7-hydroxyoct-2-enoate
• CAS: 263369-07-9
• 化学式: C₂₅H₃₄O₄Si
• 分子量: 426.628
• InChiKey: YRFARSLNOTYRJE-LOCUBWQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 碘 、 1-chloro-3-hydroxy-1,1,3,3-tetrabutyldistannoxane 、 三乙胺 、 苯甲酸 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 151.5h， 生成 (-)-(6R,14R,12S,3E,9E)-6,14-dimethyl-12-hydroxy-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：

  (4R,6R)-4-羟基-6-甲基四氢-2H-吡喃-2-酮 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 61.0h， 生成 methyl (+)-(5S,7R,2E)-5-(tert-butyldiphenylsilyloxy)-7-hydroxyoctenoate
  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).