[(1S,2R,3S,4S,4aS,11bR)-1,2,4,7-tetraacetyloxy-11b-hydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-3-yl] acetate | 935853-69-3

• 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: [(1S,2R,3S,4S,4aS,11bR)-1,2,4,7-tetraacetyloxy-11b-hydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-3-yl] acetate
• CAS: 935853-69-3
• 化学式: C₂₄H₂₅NO₁₄
• 分子量: 551.461
• InChiKey: YTQWNPMTQIZQCA-QCMHYMCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3S,4S,4aS,11bR)-1,2,4,7-tetraacetyloxy-11b-hydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-3-yl] acetate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 8.5h， 生成 [(1R,2S,3S,4S,4aR,11bS)-2,3,4-triacetyloxy-7-hydroxy-6-oxo-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] acetate
  参考文献：
  名称：

  Antineoplastic Agents. 550. Synthesis of 10b(S)-Epipancratistatin from (+)-Narciclasine^,1

  摘要：

  By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.

  DOI：

  10.1021/np068046e
• 作为产物：
  描述：

  乙酸酐 、 2,3,4,7-tetraacetoxy-10b-(R)-hydroxypancratistatin 以 吡啶 为溶剂， 反应 6.0h， 以82%的产率得到[(1S,2R,3S,4S,4aS,11bR)-1,2,4,7-tetraacetyloxy-11b-hydroxy-6-oxo-1,2,3,4,4a,5-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-3-yl] acetate
  参考文献：
  名称：

  Antineoplastic Agents. 550. Synthesis of 10b(S)-Epipancratistatin from (+)-Narciclasine^,1

  摘要：

  By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.

  DOI：

  10.1021/np068046e

文献信息

• Antineoplastic Agents. 550. Synthesis of 10b(<i>S</i>)-Epipancratistatin from (+)-Narciclasine^,1
  作者：George R. Pettit、Noeleen Melody、Delbert L. Herald、John C. Knight、Jean-Charles Chapuis

  DOI：10.1021/np068046e

  日期：2007.3.1

  By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.