[(1R,2S,3S,4S,4aR,11bR)-2,3,4-triacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] acetate | 181225-16-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: [(1R,2S,3S,4S,4aR,11bR)-2,3,4-triacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] acetate
• CAS: 181225-16-1
• 化学式: C₃₀H₃₁NO₁₂
• 分子量: 597.576
• InChiKey: TZZVOZOAXBNZLC-VUTJFYCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(1R,2S,3S,4S,4aR,11bR)-2,3,4-triacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] acetate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 以83%的产率得到(1R,2S,3S,4S,4aR,11bR)-1,2,3,4-Tetraacetoxy-1,3,4,4a,5,11b-hexahydro<1,3>dioxolo<4,5-j>phenanthridin-6(2H)-on
  参考文献：
  名称：

  Total Synthesis of (+)-7-Deoxypancratistatin and (+)-7-Deoxy-trans-dihydronarciclasine

  摘要：

  The chiral and stereoselective synthesis of antimitotic phenanthridone alkaloids, (+)-7-deoxypancratistatin (1) and (+)-7-deoxy-trans-dihydronarciclasine (2) is described. Both natural products were synthesized from the common compound (4), which had been prepared from D-glucose and employed for the synthesis of lycoricidine (3).

  DOI：

  10.3987/com-96-7481
• 作为产物：
  描述：

  [(2S,3R,4S,4aR,11bR)-3,4-bis(methoxymethoxy)-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate 在 盐酸 、 phosphate buffer 、 18-冠醚-6 、 sodium methylate 、 potassium acetate 、 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成 [(1R,2S,3S,4S,4aR,11bR)-2,3,4-triacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] acetate
  参考文献：
  名称：

  Total Synthesis of (+)-7-Deoxypancratistatin and (+)-7-Deoxy-trans-dihydronarciclasine

  摘要：

  The chiral and stereoselective synthesis of antimitotic phenanthridone alkaloids, (+)-7-deoxypancratistatin (1) and (+)-7-deoxy-trans-dihydronarciclasine (2) is described. Both natural products were synthesized from the common compound (4), which had been prepared from D-glucose and employed for the synthesis of lycoricidine (3).

  DOI：

  10.3987/com-96-7481