CbzNH-N(Cbz)bAla(2R-OH,3S-Bn)-OEt | 412941-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: CbzNH-N(Cbz)bAla(2R-OH,3S-Bn)-OEt
• 英文别名: ethyl (2R,3S)-2-hydroxy-4-phenyl-3-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]butanoate
• CAS: 412941-20-9
• 化学式: C₂₈H₃₀N₂O₇
• 分子量: 506.555
• InChiKey: LMQLNXPLQNAHNV-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  CbzNH-N(Cbz)bAla(2R-OH,3S-Bn)-OEt 在 镍 4-二甲氨基吡啶 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (2R,3S)-N-(tert-butoxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active syn-β-Amino-α-hydroxy Esters

  摘要：

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.

  DOI：

  10.1021/ja0175486
• 作为产物：
  描述：

  2-氧代-4-苯基丁酸乙酯 在 Cu((R,R)-Ph-box)(OTf)2 、 L-Selectride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 CbzNH-N(Cbz)bAla(2R-OH,3S-Bn)-OEt
  参考文献：
  名称：

  Catalytic Asymmetric Direct α-Amination Reactions of 2-Keto Esters:  A Simple Synthetic Approach to Optically Active syn-β-Amino-α-hydroxy Esters

  摘要：

  The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of the reaction is demonstrated by the direct amination of a series of 2-keto esters having different substituent patterns. The reaction provides an easy catalytic route to optically active syn-beta-amino-alpha-hydroxy esters, as demonstrated for the synthesis of masked syn-beta-amino-alpha-hydroxy esters (as oxazolidinones) and N-Boc-syn-beta-amino-alpha-hydroxy esters. On the basis of the absolute configuration of the products a tentative model for the transition state is suggested.

  DOI：

  10.1021/ja0175486