(1S,5R,6S,7R,3'R)-7-[(tert-butyl)dimethylsiloxy]-6-[(E)-3'-(tert-butyl)dimethylsiloxyoct-1'-en-1'-yl]-2-oxabicyclo[3.3.0]octan-3-one | 249890-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R,6S,7R,3'R)-7-[(tert-butyl)dimethylsiloxy]-6-[(E)-3'-(tert-butyl)dimethylsiloxyoct-1'-en-1'-yl]-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: (3aR,4S,5R,6aS)-5-[tert-butyl(dimethyl)silyl]oxy-4-[(E,3R)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 249890-44-6
• 化学式: C₂₇H₅₂O₄Si₂
• 分子量: 496.878
• InChiKey: BXHANKRFUJCMSW-KLOVHWLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5R,6S,7R,3'R)-7-[(tert-butyl)dimethylsiloxy]-6-[(E)-3'-(tert-butyl)dimethylsiloxyoct-1'-en-1'-yl]-2-oxabicyclo[3.3.0]octan-3-one 在 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 苯 为溶剂， 反应 60.5h， 生成 methyl (Z)-7-[(1R,2S,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
  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 platinum(IV) oxide 吡啶 、 2,6-二甲基吡啶 、 lead(IV) acetate 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 samarium diiodide 、 cerium(III) chloride 、 草酰氯 、 D-(-)-酒石酸二乙酯 、 氢气 、 cobalt(II) acetate 、 lithium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 氯苯 为溶剂， -78.0~125.0 ℃ 、413.68 kPa 条件下， 反应 21.91h， 生成 (1S,5R,6S,7R,3'R)-7-[(tert-butyl)dimethylsiloxy]-6-[(E)-3'-(tert-butyl)dimethylsiloxyoct-1'-en-1'-yl]-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.