{(S)-1-[(S)-2-((S)-1-Hydroxymethyl-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester | 143961-92-6

• 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: {(S)-1-[(S)-2-((S)-1-Hydroxymethyl-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester
• 英文别名: Cbz-Val-Pro-Val-ol；benzyl N-[(2S)-1-[(2S)-2-[[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 143961-92-6
• 化学式: C₂₃H₃₅N₃O₅
• 分子量: 433.548
• InChiKey: WOCMJHHMRBNNDJ-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(S)-2-((S)-1-Hydroxymethyl-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester 在 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 {(S)-2-Methyl-1-[(S)-2-(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  A method for the stereoselective synthesis of peptidyl trifluoromethyl ketones

  摘要：

  A method is described for the stereoselective preparation of peptidyl trifluoromethyl ketones which is centered around the addition of trifluoromethyl zinc iodide to a peptidyl aldehyde. Oxidation of the resulting alcohol with selected oxidants affords the corresponding ketone in greater than 99% isomeric purity.

  DOI：

  10.1016/s0040-4039(00)74238-9
• 作为产物：
  描述：

  L-缬氨酸 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 氯甲酸异丁酯 作用下， 生成 {(S)-1-[(S)-2-((S)-1-Hydroxymethyl-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  A method for the stereoselective synthesis of peptidyl trifluoromethyl ketones

  摘要：

  A method is described for the stereoselective preparation of peptidyl trifluoromethyl ketones which is centered around the addition of trifluoromethyl zinc iodide to a peptidyl aldehyde. Oxidation of the resulting alcohol with selected oxidants affords the corresponding ketone in greater than 99% isomeric purity.

  DOI：

  10.1016/s0040-4039(00)74238-9

文献信息

• A method for the stereoselective synthesis of peptidyl trifluoromethyl ketones
  作者：Philip D. Edwards

  DOI：10.1016/s0040-4039(00)74238-9

  日期：1992.7

  A method is described for the stereoselective preparation of peptidyl trifluoromethyl ketones which is centered around the addition of trifluoromethyl zinc iodide to a peptidyl aldehyde. Oxidation of the resulting alcohol with selected oxidants affords the corresponding ketone in greater than 99% isomeric purity.