methyl (2R)-2-[amino(phenylmethoxycarbonyl)amino]propanoate | 929720-24-1

• 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: methyl (2R)-2-[amino(phenylmethoxycarbonyl)amino]propanoate
• CAS: 929720-24-1
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: GMESADPSICUEFA-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[amino(phenylmethoxycarbonyl)amino]propanoate 、 N-(9-fluorenylmethoxycarbonyl)-L-alanyl fluoride 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到methyl (2R)-2-[[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]-phenylmethoxycarbonylamino]propanoate
  参考文献：
  名称：

  Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α-hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters

  摘要：

  The preparation of chiral orthogonally protected N-alpha-Z, N-beta-Fmoc- or Boc-alpha-hydrazinoacids derivatives, directly suitable for SPPS, is described in six steps with good yields starting from the corresponding alpha-aminoacids. The coupling reaction assays performed in liquid phase between N-alpha-Z-hydrazinoesters and N-Fmoc-alpha-aminoacids demonstrated the low reactivity of the hydrazinoester derivatives. However, we found that the acid fluoride method allowed the formation of hydrazinodipeptides almost quantitatively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.085
• 作为产物：
  描述：

  (R)-N-benzyloxycarbonyl-N-phthalimidoalanine methyl ester 在 盐酸 、 4-二甲氨基吡啶 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 methyl (2R)-2-[amino(phenylmethoxycarbonyl)amino]propanoate
  参考文献：
  名称：

  Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α-hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters

  摘要：

  The preparation of chiral orthogonally protected N-alpha-Z, N-beta-Fmoc- or Boc-alpha-hydrazinoacids derivatives, directly suitable for SPPS, is described in six steps with good yields starting from the corresponding alpha-aminoacids. The coupling reaction assays performed in liquid phase between N-alpha-Z-hydrazinoesters and N-Fmoc-alpha-aminoacids demonstrated the low reactivity of the hydrazinoester derivatives. However, we found that the acid fluoride method allowed the formation of hydrazinodipeptides almost quantitatively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.085

文献信息

• Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α-hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters
  作者：Isabelle Bouillon、Nicolas Brosse、Régis Vanderesse、Brigitte Jamart-Grégoire

  DOI：10.1016/j.tet.2006.12.085

  日期：2007.3

  The preparation of chiral orthogonally protected N-alpha-Z, N-beta-Fmoc- or Boc-alpha-hydrazinoacids derivatives, directly suitable for SPPS, is described in six steps with good yields starting from the corresponding alpha-aminoacids. The coupling reaction assays performed in liquid phase between N-alpha-Z-hydrazinoesters and N-Fmoc-alpha-aminoacids demonstrated the low reactivity of the hydrazinoester derivatives. However, we found that the acid fluoride method allowed the formation of hydrazinodipeptides almost quantitatively. (c) 2007 Elsevier Ltd. All rights reserved.