(+)-(18'S)-4'-desethyl-4'-deshydroxy-6'-allyl-7',8'-bisnorvinblastine | 131176-68-6

• 分子结构分类: 有机化合物
• 英文名称: (+)-(18'S)-4'-desethyl-4'-deshydroxy-6'-allyl-7',8'-bisnorvinblastine
• 英文别名: methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-4-[(2S)-2-(1H-indol-2-yl)-1-methoxy-1-oxo-3-[(3S)-1-prop-2-enylpiperidin-3-yl]propan-2-yl]-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
• CAS: 131176-68-6
• 化学式: C₄₅H₅₆N₄O₈
• 分子量: 780.962
• InChiKey: ULDNRCHUAUYPHS-AEDKFEIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+)-(18'S)-4'-desethyl-4'-deshydroxy-6'-allyl-7',8'-bisnorvinblastine 在 Proton Sponge 、 1-氯乙基氯甲酸酯 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 30.0h， 生成 (+)-(18'S)-4'-desethyl-4'-deshydroxy-7'-norvinblastine
  参考文献：
  名称：

  Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine

  摘要：

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.

  DOI：

  10.1021/jo00003a045
• 作为产物：
  描述：

  ((R)-哌啶-3-基)甲醇 在 盐酸 、 甲醇 、 sodium naphthalenide 、 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 丙酮 为溶剂， 反应 35.5h， 生成 (+)-(18'S)-4'-desethyl-4'-deshydroxy-6'-allyl-7',8'-bisnorvinblastine
  参考文献：
  名称：

  Synthesis of the vinblastine-like antitumor bis-indole alkaloid navelbine analog desethyldihydronavelbine

  摘要：

  (R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13. Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R). Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19. Only the natural 18'-epimer exhibited any antitumor activity.

  DOI：

  10.1021/jo00003a045