(4R)-4-amino-N-benzyl-4-[diethoxymethyl(ethoxy)phosphoryl]butanamide | 1446422-57-6

• 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: (4R)-4-amino-N-benzyl-4-[diethoxymethyl(ethoxy)phosphoryl]butanamide
• CAS: 1446422-57-6
• 化学式: C₁₈H₃₁N₂O₅P
• 分子量: 386.428
• InChiKey: DELQMOPTWCONJR-DIERRCTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-L-苯丙氨酸 、 (4R)-4-amino-N-benzyl-4-[diethoxymethyl(ethoxy)phosphoryl]butanamide 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以44%的产率得到tert-butyl N-[(2S)-1-[[(1R)-4-(benzylamino)-1-[diethoxymethyl(ethoxy)phosphoryl]-4-oxobutyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Enantioselective Synthesis of H-Phosphinic Acids Bearing Natural Amino Acid Residues

  摘要：

  The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butane-sulfinyl imines. Good yields and moderate to high enantiose-lectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the alpha-aminophosphinates to oligopetides were reported.

  DOI：

  10.1021/jo400798f
• 作为产物：
  描述：

  ethyl diethoxymethylphosphinate 在 rubidium carbonate 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 49.25h， 生成 (4R)-4-amino-N-benzyl-4-[diethoxymethyl(ethoxy)phosphoryl]butanamide
  参考文献：
  名称：

  Enantioselective Synthesis of H-Phosphinic Acids Bearing Natural Amino Acid Residues

  摘要：

  The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butane-sulfinyl imines. Good yields and moderate to high enantiose-lectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the alpha-aminophosphinates to oligopetides were reported.

  DOI：

  10.1021/jo400798f

文献信息

• Enantioselective Synthesis of <i>H</i>-Phosphinic Acids Bearing Natural Amino Acid Residues
  作者：Qiuli Yao、Chengye Yuan

  DOI：10.1021/jo400798f

  日期：2013.7.19

  The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butane-sulfinyl imines. Good yields and moderate to high enantiose-lectivities were obtained. Reliable methods were developed for the elucidation of the stereochemistry of these phosphinic acids and derivatives thereof. The transformation of the side chains of these analogues was studied. Methods for the conversion of the alpha-aminophosphinates to oligopetides were reported.