13-acetamido-N-[(2S)-1-(cyclohexylamino)-1-oxo-3-phenylpropan-2-yl]pentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene-13-carboxamide

• 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: 13-acetamido-N-[(2S)-1-(cyclohexylamino)-1-oxo-3-phenylpropan-2-yl]pentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene-13-carboxamide
• 化学式: C₄₁H₄₁N₃O₃
• 分子量: 623.795
• InChiKey: UQWKZSZTENNPAQ-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  47
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 78.0h， 生成 13-acetamido-N-[(2S)-1-(cyclohexylamino)-1-oxo-3-phenylpropan-2-yl]pentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene-13-carboxamide
  参考文献：
  名称：

  Practical resolution of an atropoisomeric α,α-disubstituted glycine with l-phenylalanine cyclohexylamide as chiral auxiliary

  摘要：

  L-Phenylalanine cyclohexylamide has been used as a chiral auxiliary for the medium-scale resolution of 2',1':1,2;1 ",2 ":3,4-dinaphthcyciohepta- 1,3-diene-6-amino-6-carboxylic acid (Bin), an alpha,alpha-disubstituted glycine with only axial dissymmetry. Coupling of X-Bin-OH (X=Ac; Bz) with H-(L)-Phe-NH-C6H11 by the EDC/HOBt method gave the dipeptide diastereoisomers X-(R)-Bin-(L)-Phe-NH-C6H11 and X-(S)-Bin-(L)-Phe-NH-C6H11, which were separated by crystallization (X=Bz) and/or chromatography. Extensive acidic hydrolysis, followed by esterification of the resulting free amino acid enantiomers, led to enantiomerically pure (-)-(R)-H-Bin-OMe and (+)-(S)-H-Bin-OMe with high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00253-5

文献信息

• Practical resolution of an atropoisomeric α,α-disubstituted glycine with l-phenylalanine cyclohexylamide as chiral auxiliary
  作者：Jean-Paul Mazaleyrat、Aurelia Boutboul、Yann Lebars、Anne Gaucher、Michel Wakselman

  DOI：10.1016/s0957-4166(98)00253-5

  日期：1998.8

  L-Phenylalanine cyclohexylamide has been used as a chiral auxiliary for the medium-scale resolution of 2',1':1,2;1 ",2 ":3,4-dinaphthcyciohepta- 1,3-diene-6-amino-6-carboxylic acid (Bin), an alpha,alpha-disubstituted glycine with only axial dissymmetry. Coupling of X-Bin-OH (X=Ac; Bz) with H-(L)-Phe-NH-C6H11 by the EDC/HOBt method gave the dipeptide diastereoisomers X-(R)-Bin-(L)-Phe-NH-C6H11 and X-(S)-Bin-(L)-Phe-NH-C6H11, which were separated by crystallization (X=Bz) and/or chromatography. Extensive acidic hydrolysis, followed by esterification of the resulting free amino acid enantiomers, led to enantiomerically pure (-)-(R)-H-Bin-OMe and (+)-(S)-H-Bin-OMe with high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.