9-((8S)-12,12-dimethyl-8,10-dioxolanyl)-11-demethyl-(2′,3′,4′,6′-O-tetrapivaloyl)secologanol | 1608501-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 9-((8S)-12,12-dimethyl-8,10-dioxolanyl)-11-demethyl-(2′,3′,4′,6′-O-tetrapivaloyl)secologanol
• CAS: 1608501-33-2
• 化学式: C₃₉H₆₂O₁₆
• 分子量: 786.912
• InChiKey: HDGHBXBSPLTONA-OOWXIANXSA-N

反应信息

• 作为产物：
  描述：

  9-((8R)-12,12-dimethyl-8,10-dioxolanyl)-perpivaloylsweroside 在 sodium trimethylsilanolate 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 以65%的产率得到9-((8S)-12,12-dimethyl-8,10-dioxolanyl)-11-demethyl-(2′,3′,4′,6′-O-tetrapivaloyl)secologanol
  参考文献：
  名称：

  Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives

  摘要：

  Mild and chemoselective opening of lactones with sodium trimethylsilanolate in high yields and aprotic solvents is described. Kinetic studies demonstrate that the B(Ac)2 mechanistic pathway is followed. Nucleophilic attack of silanolate onto the carbonyl of the lactone moiety is the rate-determining step. NaOH present as an impurity accelerates the reaction. The method was further applied to the base-sensitive and stable lactones derived from highly functionalized iridoid derivatives.

  DOI：

  10.1021/jo500220h