((1S,2R,3R,4S)-1-Benzyl-4-dibenzylamino-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester | 161022-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((1S,2R,3R,4S)-1-Benzyl-4-dibenzylamino-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester
• CAS: 161022-75-9
• 化学式: C₃₈H₄₆N₂O₄
• 分子量: 594.794
• InChiKey: PJNBVGKAQKZCIK-SKXFTCKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  44.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  82.03
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((1S,2R,3R,4S)-1-Benzyl-4-dibenzylamino-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 ((1S,2R,3R,4S)-4-Amino-1-benzyl-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Addition of dilithiated methyl-3-aminobutanoate to aldehydes proceeds with ul-1,2-induction

  摘要：

  Syntheses of 2-substituted 1-hydroxyethylene building blocks, useful as the central moiety of HIV-1 protease inhibitors, is described. Dilithiated N-protected-3-amino-4-phenylbutanoic methyl esters are reacted with aldehydes to give predominantly aldol products with 1,u configuration. The diastereomeric ratio depends on the N-protecting group and on the experimental conditions. The configurations are assigned by H-1-NMR of cyclic derivatives and are supported by X-ray structure.

  DOI：

  10.1016/s0040-4039(00)76697-4
• 作为产物：
  描述：

  methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 13.17h， 生成 ((1S,2R,3R,4S)-1-Benzyl-4-dibenzylamino-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Addition of dilithiated methyl-3-aminobutanoate to aldehydes proceeds with ul-1,2-induction

  摘要：

  Syntheses of 2-substituted 1-hydroxyethylene building blocks, useful as the central moiety of HIV-1 protease inhibitors, is described. Dilithiated N-protected-3-amino-4-phenylbutanoic methyl esters are reacted with aldehydes to give predominantly aldol products with 1,u configuration. The diastereomeric ratio depends on the N-protecting group and on the experimental conditions. The configurations are assigned by H-1-NMR of cyclic derivatives and are supported by X-ray structure.

  DOI：

  10.1016/s0040-4039(00)76697-4