(1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one | 249890-38-8

• 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: (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: benzyl (E)-3-[(1S,2S,4R,6S)-8-oxo-3,7-dioxatricyclo[4.3.0.02,4]nonan-2-yl]prop-2-enoate
• CAS: 249890-38-8
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: QJCJQHFKPKHEIC-LNASKWMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one 在 2,6-二甲基吡啶 、 samarium diiodide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 (1S,5R,7R,2'R,S,3'R,S)-7-[(tert-butyl)dimethylsiloxy]-6-[(E,Z)-3'-(tert-butyl)dimethylsiloxyoct-2'-carbobenzyloxy-1'-ylidene]-2-oxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of 12-epi-PGF_2α and 12,15-diepi-PGF_2α

  摘要：

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.

  DOI：

  10.1021/jo990906r
• 作为产物：
  描述：

  (1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 cerium(III) chloride 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.33h， 生成 (1S,5S,6S,7R)-6,7-epoxy-6-[(E)-2'-carbobenzyloxy-1'-vinyl]-2-oxabicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Enantioselective Synthesis of 12-epi-PGF_2α and 12,15-diepi-PGF_2α

  摘要：

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.

  DOI：

  10.1021/jo990906r

文献信息

• Enantioselective Synthesis of 12-<i>epi</i>-PGF₂_α and 12,15-<i>diepi</i>-PGF₂_α
  作者：Sheng Lai、Dongreyoul Lee、Jong Sun U、Jin Kun Cha

  DOI：10.1021/jo990906r

  日期：1999.9.1

  An enantioselective synthesis of 12-epi-PGF(2 alpha), (3) and 12,15-diepi-PGF(2 alpha) (4), PG-like compounds that are probably generated in vivo by nonenzymatic, free-radical-induced peroxidation of arachidonic acid, has been achieved starting from the commercially available Corey lactone (9). The key strategy involves SmI2 reduction of the gamma,delta-epoxy-alpha,beta-unsaturated ester 7, followed by in situ trapping with hexanal; subsequent hydrogenation and decarboxylation affords the stereoselective construction of the lower side chain. This new method is expected to provide a convenient access to various PG-like isoprostanes derived from oxidation of arachidonic acid and cis-4,7,10,13,16,19-docosahexaenoic acid.