5-O-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4-acetyloxy-2-benzoyloxy-1,13-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-16-yl] 3-O-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate | 159262-91-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-O-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4-acetyloxy-2-benzoyloxy-1,13-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-16-yl] 3-O-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 159262-91-6
• 化学式: C₄₆H₅₅NO₁₃
• 分子量: 829.942
• InChiKey: XJERGONDWMEJDN-DFYMZHAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  60
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-O-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4-acetyloxy-2-benzoyloxy-1,13-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-16-yl] 3-O-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate 在 甲酸 作用下， 反应 1.0h， 生成 [(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4-acetyloxy-16-[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy-1,13-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-2-yl] benzoate
  参考文献：
  名称：

  Improved access to 19-nor-7β, 8β-methylene-taxoids and formation of a 7-membered C-ring analog of doxetaxel by electrochemistry

  摘要：

  A new route to semisynthetic 19-nor-7 beta, 8 beta-methylene taxoids, such as compound 8, from the 7-O-trifluoromethanesulfonyl derivative 6 is reported. Evidence for a dissociation of the triflate to form a carbocation at C-7 under the reaction conditions is presented. Electrochemical reduction of the cyclopropane taxoid 8 gives, besides the expected 10-dehydroxy-cyclopropane analog 10, the 7-membered C-ring derivative 11.

  DOI：

  10.1016/0040-4039(94)88367-x
• 作为产物：
  描述：

  (4S,5R)-2,2-二甲基-4-苯基-3-叔丁氧基羰基-3,5-氧氮杂环戊烷甲酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 5-O-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4-acetyloxy-2-benzoyloxy-1,13-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.03,11.04,7.09,11]octadec-14-en-16-yl] 3-O-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  Improved access to 19-nor-7β, 8β-methylene-taxoids and formation of a 7-membered C-ring analog of doxetaxel by electrochemistry

  摘要：

  A new route to semisynthetic 19-nor-7 beta, 8 beta-methylene taxoids, such as compound 8, from the 7-O-trifluoromethanesulfonyl derivative 6 is reported. Evidence for a dissociation of the triflate to form a carbocation at C-7 under the reaction conditions is presented. Electrochemical reduction of the cyclopropane taxoid 8 gives, besides the expected 10-dehydroxy-cyclopropane analog 10, the 7-membered C-ring derivative 11.

  DOI：

  10.1016/0040-4039(94)88367-x