N-Cbz-D-Threonyl-L-alanine tert-butyl ester | 162553-97-1

• 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: N-Cbz-D-Threonyl-L-alanine tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[[(2R,3S)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoate
• CAS: 162553-97-1
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: MYIXZQKFOPLLPW-KCQAQPDRSA-N

物化性质

• 沸点：
  570.0±50.0 °C(predicted)
• 密度：
  1.173±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Cbz-D-Threonyl-L-alanine tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (S)-2-((2R,3S)-2-Amino-3-hydroxy-butyrylamino)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of the Peptide Fragment of Pseudobactin

  摘要：

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.

  DOI：

  10.1021/jo00112a009
• 作为产物：
  描述：

  氯甲酸苄酯 在 碳酸氢钠 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 N-Cbz-D-Threonyl-L-alanine tert-butyl ester
  参考文献：
  名称：

  Synthesis of the Peptide Fragment of Pseudobactin

  摘要：

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.

  DOI：

  10.1021/jo00112a009

文献信息

• Synthesis of the Peptide Fragment of Pseudobactin
  作者：John F. Okonya、Teodozyj Kolasa、Marvin J. Miller

  DOI：10.1021/jo00112a009

  日期：1995.4

  Synthesis of the peptide fragment, L-Lys-D-threo-beta-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported. By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups. To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala . O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent. Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.