(3R,4S)-bis-N,O-triethylsilyl-4-(2-methylpropyl)-3-hydroxy-azetidin-2-one | 313221-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-bis-N,O-triethylsilyl-4-(2-methylpropyl)-3-hydroxy-azetidin-2-one
• 英文别名: (3R,4S)-4-(2-methylpropyl)-1-triethylsilyl-3-triethylsilyloxyazetidin-2-one
• CAS: 313221-85-1
• 化学式: C₁₉H₄₁NO₂Si₂
• 分子量: 371.711
• InChiKey: DOYDEJFBDPXQQB-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-bis-N,O-triethylsilyl-4-(2-methylpropyl)-3-hydroxy-azetidin-2-one 在 4-二甲氨基吡啶 、 potassium fluoride 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 (3R,4S)-1-(tert-butyloxycarbonyl)-3-triethylsilyloxy-4-(2-methylpropyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis of the C-13 Side Chain Precursors of the 9-Dihydrotaxane Analogue ABT-271

  摘要：

  [GRAPHICS]N-Boc-L-Leucinol was converted to two C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271. The trans-oxazolidine acid 4 and the cis-Boc-lactam 2b were prepared in 44% and 40% overall yield, respectively, and with excellent (>98%) stereochemical purity.

  DOI：

  10.1021/ol006508o
• 作为产物：
  描述：

  iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate 在 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (3R,4S)-bis-N,O-triethylsilyl-4-(2-methylpropyl)-3-hydroxy-azetidin-2-one
  参考文献：
  名称：

  An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271

  摘要：

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.

  DOI：

  10.1021/jo0057203

文献信息

• Synthesis of the C-13 Side Chain Precursors of the 9-Dihydrotaxane Analogue ABT-271
  作者：M. Robert Leanna、John A. DeMattei、Wenke Li、Paul J. Nichols、Michael Rasmussen、Howard E. Morton

  DOI：10.1021/ol006508o

  日期：2000.11.1

  [GRAPHICS]N-Boc-L-Leucinol was converted to two C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271. The trans-oxazolidine acid 4 and the cis-Boc-lactam 2b were prepared in 44% and 40% overall yield, respectively, and with excellent (>98%) stereochemical purity.
• An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271
  作者：John A. DeMattei、M. Robert Leanna、Wenke Li、Paul J. Nichols、Michael W. Rasmussen、Howard E. Morton

  DOI：10.1021/jo0057203

  日期：2001.5.1

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.