(E)-(2S,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1(18),8,15(19),16-tetraen-14-one | 211692-06-7

• 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-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1(18),8,15(19),16-tetraen-14-one
• 英文别名: (2S,5R,6S,8E)-6-phenylmethoxy-3,13,20-trioxatricyclo[13.2.2.12,5]icosa-1(18),8,15(19),16-tetraen-14-one
• CAS: 211692-06-7
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: KCKZLGKDGVMJSI-RVIZHTOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2S,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1(18),8,15(19),16-tetraen-14-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,8S,9S)-6-Benzyloxy-8,9-dihydroxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1(18),15(19),16-trien-14-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：

  (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal 在 4-二甲氨基吡啶 、 lithium hydroxide 、 lithium aluminium tetrahydride 、 4 A molecular sieve 、 2,4,6-三氯苯甲酰氯 、 水 、 对甲苯磺酸 、 溶剂黄146 、 丙酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (E)-(2S,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1(18),8,15(19),16-tetraen-14-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

文献信息

• Ansa Macrolides as Molecular Workbenches: Stereocontrolledsyn Additions toE olefins
  作者：Johann Mulzer、Karin Schein、Jan W. Bats、Jürgen Buschmann、Peter Luger

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

  日期：1998.6.19

  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.