4-benzyl-3-benzyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester | 412941-09-4

• 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: 4-benzyl-3-benzyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester
• 英文别名: methyl (4S,5R)-4-benzyl-2-oxo-3-(phenylmethoxycarbonylamino)-1,3-oxazolidine-5-carboxylate
• CAS: 412941-09-4
• 化学式: C₂₀H₂₀N₂O₆
• 分子量: 384.389
• InChiKey: XKBWOORSJREHFQ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzyl-3-benzyloxycarbonylamino-2-oxazolidinone-5-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 生成 (4S,5R)-4-苄基-2-恶唑烷酮-5-羧酸甲酯
  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 sodium hydroxide 、 Cu((R,R)-Ph-box)(OTf)2 、 L-Selectride 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 4-benzyl-3-benzyloxycarbonylamino-2-oxazolidinone-5-carboxylic 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