3-O-tert-butyl 5-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S,16S)-4,12-diacetyloxy-2-benzoyloxy-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-15-yl] (4R,5R)-2-(2,4-dimethoxyphenyl)-4-(2-methylpropyl)-1,3-oxazolidine-3,5-dicarboxylate | 777950-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-O-tert-butyl 5-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S,16S)-4,12-diacetyloxy-2-benzoyloxy-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-15-yl] (4R,5R)-2-(2,4-dimethoxyphenyl)-4-(2-methylpropyl)-1,3-oxazolidine-3,5-dicarboxylate
• CAS: 777950-78-4
• 化学式: C₅₄H₆₇NO₁₈
• 分子量: 1018.12
• InChiKey: WFOBRIARFQMUIL-XWPLMQQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  73
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  235
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  3-O-tert-butyl 5-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S,16S)-4,12-diacetyloxy-2-benzoyloxy-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-15-yl] (4R,5R)-2-(2,4-dimethoxyphenyl)-4-(2-methylpropyl)-1,3-oxazolidine-3,5-dicarboxylate 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S,16S)-4,12-diacetyloxy-9-hydroxy-15-[(2R,3R)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]oxy-10,14,20,20-tetramethyl-11,18-dioxo-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-2-yl] benzoate
  参考文献：
  名称：

  New Taxane Derivatives:  Synthesis of Baccatin[14,1-d]furan-2-one Nucleus and Its Condensation with the Norstatine Side Chain

  摘要：

  New taxanes 15 and 18, containing the unsaturated and saturated baccatin[14,1-d]furan-2-one nucleus, respectively, were prepared starting from the readily available 13-oxo-7-Tes-baccatin III (3). Sequential formation of the enolate of 3 and reaction with ethyl glyoxylate gave the 13-oxo-7-Tes-baccatin[14,1-d]-3,4-dehydrofuran-2-one 4. The reduction of 4 can result in the formation of a mixture of compounds corresponding to 13-hydroxy alcohol 5 and 13-enol derivative 6. Both 5 and 6 were transformed into 13-oxo-7-Tes-baccatin[14,1-d]furan-2-one 8 by treatment with a base. Further reduction of 8 gave 13-hydroxy compound 9. Esterification of 6 and 9 with NO-protected norstatine 12, followed by deprotection, gave the new promising anticancer taxanes 15 and 18, respectively.

  DOI：

  10.1021/jo0493018
• 作为产物：
  描述：

  [(1R,2S,3R,4S,7R,9S,10S,12R)-4,12-diacetyloxy-10,14,20,20-tetramethyl-11,15,18-trioxo-9-triethylsilyloxy-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icosa-13,16-dien-2-yl] benzoate 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 sodium hydrogen sulfate 、 氢气 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 34.25h， 生成 3-O-tert-butyl 5-O-[(1S,2S,3R,4S,7R,9S,10S,12R,15S,16S)-4,12-diacetyloxy-2-benzoyloxy-9-hydroxy-10,14,20,20-tetramethyl-11,18-dioxo-6,19-dioxapentacyclo[11.6.1.01,16.03,10.04,7]icos-13-en-15-yl] (4R,5R)-2-(2,4-dimethoxyphenyl)-4-(2-methylpropyl)-1,3-oxazolidine-3,5-dicarboxylate
  参考文献：
  名称：

  New Taxane Derivatives:  Synthesis of Baccatin[14,1-d]furan-2-one Nucleus and Its Condensation with the Norstatine Side Chain

  摘要：

  New taxanes 15 and 18, containing the unsaturated and saturated baccatin[14,1-d]furan-2-one nucleus, respectively, were prepared starting from the readily available 13-oxo-7-Tes-baccatin III (3). Sequential formation of the enolate of 3 and reaction with ethyl glyoxylate gave the 13-oxo-7-Tes-baccatin[14,1-d]-3,4-dehydrofuran-2-one 4. The reduction of 4 can result in the formation of a mixture of compounds corresponding to 13-hydroxy alcohol 5 and 13-enol derivative 6. Both 5 and 6 were transformed into 13-oxo-7-Tes-baccatin[14,1-d]furan-2-one 8 by treatment with a base. Further reduction of 8 gave 13-hydroxy compound 9. Esterification of 6 and 9 with NO-protected norstatine 12, followed by deprotection, gave the new promising anticancer taxanes 15 and 18, respectively.

  DOI：

  10.1021/jo0493018