(E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1(19),9,16(20),17-tetraen-15-one | 211692-08-9

• 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: (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1(19),9,16(20),17-tetraen-15-one
• CAS: 211692-08-9
• 化学式: C₂₅H₂₈O₅
• 分子量: 408.494
• InChiKey: CRIJMHWARGTKIW-ABHFGSPXSA-N

反应信息

• 作为反应物：
  描述：

  (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1(19),9,16(20),17-tetraen-15-one 在 四氧化锇 、 N-甲基吲哚酮 、 水 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 (2S,5R,6S,9S,10S)-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 、 (2S,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：

  Benzoic acid (E)-(8S,9R)-8-benzyloxy-9,10-dihydroxy-dec-4-enyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 4 A molecular sieve 、 2,4,6-三氯苯甲酰氯 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 (E)-(2S,5R,6S)-6-Benzyloxy-3,14,21-trioxa-tricyclo[14.2.2.1^2,5]henicosa-1(19),9,16(20),17-tetraen-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