(R)-N-benzyloxycarbonyl-N-phthalimidophenylalanine methyl ester | 339201-16-0

• 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: (R)-N-benzyloxycarbonyl-N-phthalimidophenylalanine methyl ester
• 英文别名: methyl (2R)-2-[(1,3-dioxoisoindol-2-yl)-phenylmethoxycarbonylamino]-3-phenylpropanoate
• CAS: 339201-16-0
• 化学式: C₂₆H₂₂N₂O₆
• 分子量: 458.47
• InChiKey: RGXANROCRFKKAU-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-N-benzyloxycarbonyl-N-phthalimidophenylalanine methyl ester 在 4-二甲氨基吡啶 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 1-benzyl 2-(tert-butyl) (R)-1-(1-methoxy-1-oxo-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
  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：

  L-苯丙氨酸 在 dialkylazodicarboxylate 、 溶剂黄146 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (R)-N-benzyloxycarbonyl-N-phthalimidophenylalanine methyl ester
  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

• A New Synthetic Route to Protected α-Hydrazinoesters in High Optical Purity Using the Mitsunobu Protocol
  作者：Nicolas Brosse、Maria-Fatima Pinto、Jacques Bodiguel、Brigitte Jamart-Grégoire

  DOI：10.1021/jo005696t

  日期：2001.4.1
• 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.