[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-(furan-2-yl)-3-(phenylmethoxycarbonylamino)-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 288390-05-6

• 英文名称: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-(furan-2-yl)-3-(phenylmethoxycarbonylamino)-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 288390-05-6
• 化学式: C₅₈H₇₉NO₁₆Si₂
• 分子量: 1102.43
• InChiKey: RNFOTFLAHQILPB-QZBMGFLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.88
• 重原子数：
  77.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  221.66
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-(furan-2-yl)-3-(phenylmethoxycarbonylamino)-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 以59%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-amino-3-(furan-2-yl)-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Structure–activity relationships study at the 3′-N position of paclitaxel. part 2: synthesis and biological evaluation of 3′-N-thiourea- and 3′-N-thiocarbamate-bearing paclitaxel analogues

  摘要：

  The syntheses and preliminary biological evaluation of 3'-N-thiocarbamate- and 3'-N'-thiourea-bearing paclitaxel analogues, 4a-f and 5a-e, are described. 3'-N-thiocarbamates 4a-e were found to be more potent than paclitaxel in both the tubulin polymerization assay and the in vitro cytotoxicity assay. Several derivatives of this class such as 4c, 4d, and 4e also exhibited some in vivo activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00242-0
• 作为产物：
  描述：

  7-O-(三乙基硅烷基)浆果赤霉素III 、 (2R,3R)-2-Furan-2-yl-4-oxo-3-triethylsilanyloxy-azetidine-1-carboxylic acid benzyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-(furan-2-yl)-3-(phenylmethoxycarbonylamino)-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Structure–activity relationships study at the 3′-N position of paclitaxel. part 2: synthesis and biological evaluation of 3′-N-thiourea- and 3′-N-thiocarbamate-bearing paclitaxel analogues

  摘要：

  The syntheses and preliminary biological evaluation of 3'-N-thiocarbamate- and 3'-N'-thiourea-bearing paclitaxel analogues, 4a-f and 5a-e, are described. 3'-N-thiocarbamates 4a-e were found to be more potent than paclitaxel in both the tubulin polymerization assay and the in vitro cytotoxicity assay. Several derivatives of this class such as 4c, 4d, and 4e also exhibited some in vivo activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00242-0