[(2S,3R,4S,4aR,11bR)-3,4-diacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate | 181225-02-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: [(2S,3R,4S,4aR,11bR)-3,4-diacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate
• CAS: 181225-02-5
• 化学式: C₂₈H₂₉NO₁₀
• 分子量: 539.539
• InChiKey: PYKGDBAKYYLQQY-ZGUHPQOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  126.9
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,4aR,11bR)-3,4-diacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl] acetate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 以85%的产率得到(+)-2,3,4-triacetoxy-trans-dihydrolycoricidine
  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 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 [(2S,3R,4S,4aR,11bR)-3,4-diacetyloxy-5-[(4-methoxyphenyl)methyl]-6-oxo-1,2,3,4,4a,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-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