[(2S,3S,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] trifluoromethanesulfonate | 181378-99-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: [(2S,3S,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] trifluoromethanesulfonate
• CAS: 181378-99-4
• 化学式: C₂₇H₃₀F₃NO₁₁S
• 分子量: 633.597
• InChiKey: BQBIIAOJSRFNTP-XDZZJOFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  128.29
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  [(2S,3S,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] trifluoromethanesulfonate 在 18-冠醚-6 、 potassium acetate 作用下， 以 苯 为溶剂， 以81%的产率得到(3R,4S,4aR,11bR)-3,4-bis(methoxymethoxy)-5-[(4-methoxyphenyl)methyl]-3,4,4a,11b-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6-one
  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 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 [(2S,3S,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] trifluoromethanesulfonate
  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