iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate | 145761-30-4

• 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: iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate
• 英文别名: isopropyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate；nor-statine；propan-2-yl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate
• CAS: 145761-30-4
• 化学式: C₁₀H₂₁NO₃
• 分子量: 203.282
• InChiKey: GVPVMNQIAGKWDL-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate 在 4-二甲氨基吡啶 、 potassium fluoride 、 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 (3R,4S)-1-(tert-butyloxycarbonyl)-3-triethylsilyloxy-4-(2-methylpropyl)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
• 作为产物：
  描述：

  在 水 作用下， 反应 3.0h， 以10.3 g的产率得到iso-propyl (2R,3S)-3-amino-2-hydroxy-5-methylhexanoate
  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

文献信息

• Aminosäurederivate
  申请人：MERCK PATENT GmbH

  公开号：EP0474008A1

  公开（公告）日：1992-03-11

  Neue Aminosäurederivate der Formel I         X-W-CR¹R²-CO-Y-NH-CHR³-CR⁴-COOR⁵   I worin R¹ bis R⁵, W, X und Y die in Patentanspruch 1 angegebenen Bedeutungen haben, sowie ihre Salze hemmen die Aktivität des menschlichen Plasmarenins.

  式 I 的新氨基酸衍生物 X-W-CR¹R²-CO-Y-NH-CHR³-CR⁴-COR⁵ I 其中 R¹ 至 R⁵、W、X 和 Y 具有权利要求 1 中给出的含义、 及其盐类可抑制人血浆肾素的活性。
• A novel synthesis of nor-C-statine.
  作者：Robert W. Dugger、Jane L. Ralbovsky、Don Bryant、Jane Commander、Steve S. Massett、Nancy A. Sage、Joe R. Selvidio

  DOI：10.1016/s0040-4039(00)61770-7

  日期：1992.11

  A new synthesis of nor-C-statine is described. Benzylation of a malate dianion, differentiation of the two carboxylates and a Hofmann degradation of one of the carboxylates constitute the key steps of the synthesis.
• 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.
• 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.