2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lupan-28-oate | 700840-72-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lupan-28-oate
• CAS: 700840-72-8
• 化学式: C₅₈H₈₆O₂₁
• 分子量: 1119.31
• InChiKey: VSYQZUUTEKAKAF-YQAGAXSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  79.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  264.39
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lupan-28-oate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以67.2%的产率得到3β-(β-D-glucopyranosyloxy)lupan-28-oate
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34
• 作为产物：
  描述：

  3β,28-diacetoxydihydrobetuline 在 氢氧化钾 、 sodium periodate 、 四氧化钌 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lupan-28-oate
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34