(-)-(3aR,4R,5R,6R,7R,7aR)-6,7-epoxy-5-phenyl-6-tosyl-1,3,3a,4,5,6,7,7a-octahydroisobenzofuran-3a,4-diol | 1211945-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (-)-(3aR,4R,5R,6R,7R,7aR)-6,7-epoxy-5-phenyl-6-tosyl-1,3,3a,4,5,6,7,7a-octahydroisobenzofuran-3a,4-diol
• CAS: 1211945-70-8
• 化学式: C₂₁H₂₂O₆S
• 分子量: 402.468
• InChiKey: LYETVFODQBPHSD-OWQNAKTJSA-N

反应信息

• 作为反应物：
  描述：

  (-)-(3aR,4R,5R,6R,7R,7aR)-6,7-epoxy-5-phenyl-6-tosyl-1,3,3a,4,5,6,7,7a-octahydroisobenzofuran-3a,4-diol 在 magnesium 、 1,2-二溴乙烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以30%的产率得到(-)-(3aS,6R,7R,7aR)-4-7,7a-dihydroxy-6-phenylhexahydroisobenzofuran-5-(1H)-one
  参考文献：
  名称：

  Sulfoxide-Directed Intramolecular [4 + 2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes

  摘要：

  Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.

  DOI：

  10.1021/jo9024489
• 作为产物：
  描述：

  (+)-(3aR,4R,5R,7aS)-5-phenyl-6-tosyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-3a,4-diol 在 叔丁基过氧化氢 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 t-BuOO-t-Bu 为溶剂， 以55%的产率得到(-)-(3aR,4R,5R,6R,7R,7aR)-6,7-epoxy-5-phenyl-6-tosyl-1,3,3a,4,5,6,7,7a-octahydroisobenzofuran-3a,4-diol
  参考文献：
  名称：

  Sulfoxide-Directed Intramolecular [4 + 2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes

  摘要：

  Sulfinyl dienynes undergo thermal and catalyzed IMDA cycloadditions, often at room temperature, to produce cyclohexa-1,4-dienes with good yields and high selectivities. Additionally, the products preserve a synthetically useful vinyl sulfoxide functionality. The selective manipulation of the double bonds in the cycloadducts has also been examined in this work.

  DOI：

  10.1021/jo9024489