[(1S,2S,3R,4S,7R,8S,12S,13S,15R,18S)-4,15-diacetyloxy-18-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-13,17,20,20-tetramethyl-14-oxo-10-sulfanylidene-6,9,11-trioxapentacyclo[14.3.1.03,13.04,7.08,12]icos-16-en-2-yl] benzoate | 200568-21-4

• 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: [(1S,2S,3R,4S,7R,8S,12S,13S,15R,18S)-4,15-diacetyloxy-18-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-13,17,20,20-tetramethyl-14-oxo-10-sulfanylidene-6,9,11-trioxapentacyclo[14.3.1.03,13.04,7.08,12]icos-16-en-2-yl] benzoate
• CAS: 200568-21-4
• 化学式: C₅₄H₆₃NO₁₅SSi
• 分子量: 1026.24
• InChiKey: WJNPITPSAAKJGW-BXRDVACUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  72
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  241
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,8S,12S,13S,15R,18S)-4,15-diacetyloxy-18-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-13,17,20,20-tetramethyl-14-oxo-10-sulfanylidene-6,9,11-trioxapentacyclo[14.3.1.03,13.04,7.08,12]icos-16-en-2-yl] benzoate 在 盐酸 、 偶氮二异丁腈 、 tributylgermanium hydride 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 生成 6-α-hydroxy-7-deoxy paclitaxel
  参考文献：
  名称：

  Stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel

  摘要：

  The synthetic transposition of the 7-hydroxyl group of paclitaxel to the 6-position is described. The route presented prepares both the 6-alpha- and beta-isomers stereospecifically. The key step of this transposition involves the stereoselective reduction of the 6,7-alpha-thiocarbonate using tributylgermanium hydride. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00864-3
• 作为产物：
  描述：

  [(1S,2S,3R,4S,7R,10R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadeca-8,13-dien-2-yl] benzoate 在 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 [(1S,2S,3R,4S,7R,8S,12S,13S,15R,18S)-4,15-diacetyloxy-18-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-13,17,20,20-tetramethyl-14-oxo-10-sulfanylidene-6,9,11-trioxapentacyclo[14.3.1.03,13.04,7.08,12]icos-16-en-2-yl] benzoate
  参考文献：
  名称：

  Stereospecific synthesis of 7-deoxy-6-hydroxy paclitaxel

  摘要：

  The synthetic transposition of the 7-hydroxyl group of paclitaxel to the 6-position is described. The route presented prepares both the 6-alpha- and beta-isomers stereospecifically. The key step of this transposition involves the stereoselective reduction of the 6,7-alpha-thiocarbonate using tributylgermanium hydride. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00864-3