β-Benzyl D-threo-β-hydroxyaspartate | 162553-93-7

• 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: β-Benzyl D-threo-β-hydroxyaspartate
• 英文别名: (2R,3R)-2-amino-3-hydroxy-4-oxo-4-phenylmethoxybutanoic acid
• CAS: 162553-93-7
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: RMINQGRRRJVALW-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-Benzyl D-threo-β-hydroxyaspartate 在 potassium hydrogencarbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 95.0h， 生成 (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine
  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：

  (2R,3R)-2-氨基-3-羟基琥珀酸 、 苯甲醇 在 盐酸 作用下， 反应 2.0h， 以90%的产率得到β-Benzyl D-threo-β-hydroxyaspartate
  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

• N-carboxy-anhydrides derived from threo- and erythro-β-hydroxyaspartic acids and poly-β-methyl hydrogen threo-β-methoxy-<scp>DL</scp>-aspartate
  作者：Y. Liwschitz、A. Singerman

  DOI：10.1039/j39670001696

  日期：——

  The N-carboxy-anhydrides derived from either threo- or erythro-β-hydroxy-DL-Aspartic ACID In which the hydroxy-group is protected by an acetyl group and the β-carboxy-group by a benzyl or methyl ester do not undergo polymerisation in solution by basic catalysts or in bulk. This is due to an O→N-acetyl shift. Polymerisation does take place after methylation of the hydroxy-group.

  衍生自苏-或赤-β-羟基-DL-天冬氨酸的N-羧基酸酐，其中羟基被乙酰基保护而β-羧基被苄基或甲基酯保护通过碱性催化剂在溶液中或本体聚合。这是由于O → N-乙酰基转移。羟基甲基化后确实发生聚合。