4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-8-hydroxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid | 211691-94-0

• 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: 4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-8-hydroxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid
• CAS: 211691-94-0
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: DENXUVGICVIVDZ-JPLDLVEYSA-N

反应信息

• 作为反应物：
  描述：

  4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-8-hydroxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 2,4,6-三氯苯甲酰氯 、 水 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 34.0h， 生成 (2R,5R,6S,9R,10R)-6-Benzyloxy-9,10-dihydroxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1(19),16(20),17-trien-15-one
  参考文献：
  名称：

  Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins

  摘要：

  Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.

  DOI：

  10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u
• 作为产物：
  描述：

  4-[(2R,4R)-4-((E)-(S)-8-Benzoyloxy-1-benzyloxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid methyl ester 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-8-hydroxy-oct-4-enyl)-[1,3]dioxolan-2-yl]-benzoic acid
  参考文献：
  名称：

  Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins

  摘要：

  Fixed on an aromatic platform in a conformationally defined way, acyclic (E)-alkenes can be considered gripped on a molecular workbench. The olefinic ansa-macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N-methylmorpholin-N-oxide.

  DOI：

  10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u