N-Cbz-D-Glu(OEt)-NH-nPn

• 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-Cbz-D-Glu(OEt)-NH-nPn
• 英文别名: N-Cbz-D-Glu(OEt)NHPn；ethyl (4R)-5-oxo-5-(pentylamino)-4-(phenylmethoxycarbonylamino)pentanoate
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: FLOLTQQOXFDCCQ-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-氨基戊烷 、 N-Cbz-D-Glu(OEt)-OEt 在 4 A molecular sieve 、 对硝基苯甲腈 作用下， 以 异丙醚 为溶剂， 反应 48.0h， 以64%的产率得到N-Cbz-D-Glu(NH-nPn)-OEt
  参考文献：
  名称：

  Regio- and enantioselectivity of the Candida antarctica lipase catalyzed amidations of Cbz-l- and Cbz-d-glutamic acid diesters

  摘要：

  Candida antarctica lipase (CAL) catalyzed amidation of Cbz-glutamic acid diesters takes place in a regioselective way to give the corresponding monoamide derivatives. The regioselectivity was found to be dependent on the reacting Glu enantiomer. Thus, amidations of Cbz-L-Glu diesters regiospecifically afforded alpha-amide while the gamma-ester is selectively substituted in the D-enantiomer. This enzymatic reaction also shows enantioselectivity when a chiral amine is used as nucleophile.

  DOI：

  10.1016/0957-4166(95)00310-l

文献信息

• Regio- and enantioselectivity of the Candida antarctica lipase catalyzed amidations of Cbz-l- and Cbz-d-glutamic acid diesters
  作者：Cristina Chamorro、Rosario González-Muñiz、Santiago Conde

  DOI：10.1016/0957-4166(95)00310-l

  日期：1995.9

  Candida antarctica lipase (CAL) catalyzed amidation of Cbz-glutamic acid diesters takes place in a regioselective way to give the corresponding monoamide derivatives. The regioselectivity was found to be dependent on the reacting Glu enantiomer. Thus, amidations of Cbz-L-Glu diesters regiospecifically afforded alpha-amide while the gamma-ester is selectively substituted in the D-enantiomer. This enzymatic reaction also shows enantioselectivity when a chiral amine is used as nucleophile.
• Regioselective lipase-catalysed γ-monoamidation of d-glutamic acid diesters: effect of the N-protecting group
  作者：Santiago Conde、Paloma López-Serrano、Ana Martı́nez

  DOI：10.1016/s0957-4166(00)00210-x

  日期：2000.6

  N-Blocked-D-glutamic acid diethylesters are gamma-regioselectively amidated in a reaction catalysed by Candida antarctica lipase B, carried out in an anhydrous organic solvent. The ratio of gamma:alpha-monoamides, as a measure of regioselectivity, depends on the N-protecting group present in the substrate. In the examples reported in this work, we have found that gamma:alpha ranges from about 4 (N-group = Cbz) to 35 (N-group = isobutyryl). No diamides were detected. (C) 2000 Elsevier Science Ltd. All rights reserved.