digitoxigen (2,3,4,6-triacetyl-β-L-fucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside | 1426432-94-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: digitoxigen (2,3,4,6-triacetyl-β-L-fucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
• CAS: 1426432-94-1
• 化学式: C₅₃H₈₀O₂₀
• 分子量: 1037.21
• InChiKey: MZCLMQRKZLQNEU-SIXKASGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  73.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  259.96
• 氢给体数：
  4.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 、 洋地黄毒苷 在 diphenylborate ethanolamine ester 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以51%的产率得到digitoxigen (2,3,4,6-triacetyl-β-L-fucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
  参考文献：
  名称：

  Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

  摘要：

  The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea. Variation of the glycosyl donor was tolerated, enabling the synthesis of novel cardiac glycoside analogs from readily available materials.

  DOI：

  10.1021/ol4003042