digitoxigen (2,3,4,6-tetraacetyl-β-D-galactopyranosyl)-(1→3)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside | 1426432-92-9

• 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-tetraacetyl-β-D-galactopyranosyl)-(1→3)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside
• CAS: 1426432-92-9
• 化学式: C₅₅H₈₂O₂₂
• 分子量: 1095.24
• InChiKey: OGMVIKXEEGFZEL-ZUYAYJOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  77.0
• 可旋转键数：
  14.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  286.26
• 氢给体数：
  4.0
• 氢受体数：
  22.0

反应信息

• 作为产物：
  描述：

  洋地黄毒苷 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 diphenylborate ethanolamine ester 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 digitoxigen (2,3,4,6-tetraacetyl-β-D-galactopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-(2,6-dideoxy-β-D-ribohexopyranosyl)-(1→4)-2,6-dideoxy-β-D-ribohexopyranoside 、 digitoxigen (2,3,4,6-tetraacetyl-β-D-galactopyranosyl)-(1→3)-(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