(9S,13R)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinan-7-one | 160694-02-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (9S,13R)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinan-7-one
• CAS: 160694-02-0
• 化学式: C₃₃H₃₃NO₆
• 分子量: 539.628
• InChiKey: MLBNFCOVRJKMQR-OGVWKLGRSA-N

反应信息

• 作为反应物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (9S,13R)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinan-7-one 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以83%的产率得到(9S,13R)-6,7,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxy-7-<(trifluoromethanesulfonyl)oxy>morphinane
  参考文献：
  名称：

  Syntheses of Antitumor Morphinane Alkaloids, Sinococuline and 6-epi-, 7-epi-, and 6-epi-7-epi-Sinococuline, from Sinomenine

  摘要：

  An antitumor alkaloid, sinococuline (1), and its C-6 and/or C-7 epimeric analogs 3-5 have been synthesized from sinomenine (2). The carbonyl transposition from 9 to 8 using selenoxide chemistry proceeded in an efficient manner. Successive C-6 hydroxylation through the potassium enolate oxidation with (-)-(2S,8aR)-(camphorsulfonyl)oxaziridine (23) predominantly produced the beta-hydroxy enone 7a, which allowed access to sinococuline (1) and the 7-epi-analog 4. On the contrary, the oxidation of the lithium enolate with (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine (22) resulted in predominant formation of the a-hydroxy enone 7b, which was converted to the 6-epi-analogs 3 and 5. In contrast to the marked antitumor activity of 1, analogs 3-5 showed no activity.

  DOI：

  10.1021/jo00119a037
• 作为产物：
  描述：

  (9S,13S)-5,6,8,14-Tetrahydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinan-7-one 在 Wilkinson's catalyst 氢气 作用下， 以 苯 为溶剂， 反应 72.0h， 以97%的产率得到(9S,13R)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinan-7-one
  参考文献：
  名称：

  Synthesis of an antitumour alkaloid sinococuline from sinomenine

  摘要：

  抗肿瘤吗啡烯生物碱辛可可林1是通过高效的方式从辛伐美辛2合成的。

  DOI：

  10.1039/c39940002707