digitoxigen (2,3,4,6-tetracetyl-β-D-glucopyranosyl)-(1→4)-(2,3,6-triacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside | 1426432-96-3

• 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-tetracetyl-β-D-glucopyranosyl)-(1→4)-(2,3,6-triacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
• CAS: 1426432-96-3
• 化学式: C₆₇H₉₈O₃₀
• 分子量: 1383.5
• InChiKey: GCCLREWREPAZRP-HOUSWVFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  97.0
• 可旋转键数：
  20.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  383.62
• 氢给体数：
  4.0
• 氢受体数：
  30.0

反应信息

• 作为产物：
  描述：

  洋地黄毒苷 、 乙酰溴代纤维二糖 在 diphenylborate ethanolamine ester 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以74%的产率得到digitoxigen (2,3,4,6-tetracetyl-β-D-glucopyranosyl)-(1→4)-(2,3,6-triacetyl-β-D-glucopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-hexopyranosyl-(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