N_α-benzoyl-D,L-asparagine ethyl ester | 368875-00-7

• 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: N_α-benzoyl-D,L-asparagine ethyl ester
• 英文别名: N²-benzoyl-DL-asparagine ethyl ester；N²-Benzoyl-DL-asparagin-aethylester；Ethyl 4-amino-2-benzamido-4-oxobutanoate
• CAS: 368875-00-7
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: ORBYSVGYEXDIGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N_α-benzoyl-D,L-asparagine ethyl ester 在 盐酸 、 Alcalase 2.4L from Bacillus sp 、 sodium chloride 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 23.0h， 以47%的产率得到N_α-benzoyl-D-asparagine ethyl ester
  参考文献：
  名称：

  Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

  摘要：

  A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions-racemization of the retained ester and a strong enzyme inactivation-a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.118
• 作为产物：
  描述：

  N-benzoyl-aspartic acid anhydride 在 1,4-二氧六环 、 乙醇 、 氯仿 、 三乙胺 作用下， 生成 N_α-benzoyl-D,L-asparagine ethyl ester
  参考文献：
  名称：

  肽链的特定化学裂变研究。第一部分：天冬氨酰和谷氨酰胺肽的重排

  摘要：

  DOI：

  10.1039/jr9550000259

文献信息

• Studies on specific chemical fission of peptide links. Part I. The rearrangement of aspartyl and glutamyl peptides
  作者：Alan R. Battersby、J. C. Robinson

  DOI：10.1039/jr9550000259

  日期：——
• Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives
  作者：Hans Iding、Beat Wirz、Mark Rogers-Evans

  DOI：10.1016/j.tet.2003.10.118

  日期：2004.1

  A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions-racemization of the retained ester and a strong enzyme inactivation-a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates. (C) 2003 Elsevier Ltd. All rights reserved.