methyl (1S,2R,4S,5R)-2-(tert-butoxycarbonylamino)-4,5-epoxycyclohexanecarboxylate | 1321925-41-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: methyl (1S,2R,4S,5R)-2-(tert-butoxycarbonylamino)-4,5-epoxycyclohexanecarboxylate
• 英文别名: methyl (1R,3S,4R,6S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxabicyclo[4.1.0]heptane-3-carboxylate
• CAS: 1321925-41-0
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: FFGIZYMVXJKQRL-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4S,5R)-2-(tert-butoxycarbonylamino)-4,5-epoxycyclohexanecarboxylate 在 咪唑 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 methyl (1S,2R,4S,5S)-2-(tert-butoxycarbonylamino)-5-(2-chloroethoxy)-4-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate
  参考文献：
  名称：

  2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic β-peptide conjugates

  摘要：

  Oligomers of cyclic-beta-aminoacids possess a high resistance to peptidase-catalyzed hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These characteristics are attractive to develop new biologically active substances. However, cyclic-beta-peptides often show limited solubility in water and cannot be conjugated to biologically relevant fragments, such as oligosaccharides, which are often essential for full biological activity of natural alpha-peptides. In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexanecarboxylic acid (ACHC), both functionalized with a hydroxy group, to increase the solubility in water, and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a 'click reaction'. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.131
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 叠氮磷酸二苯酯 、 奎尼丁 、 三乙胺 、 间氯过氧苯甲酸 、 copper(l) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl (1S,2R,4S,5R)-2-(tert-butoxycarbonylamino)-4,5-epoxycyclohexanecarboxylate
  参考文献：
  名称：

  2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic β-peptide conjugates

  摘要：

  Oligomers of cyclic-beta-aminoacids possess a high resistance to peptidase-catalyzed hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These characteristics are attractive to develop new biologically active substances. However, cyclic-beta-peptides often show limited solubility in water and cannot be conjugated to biologically relevant fragments, such as oligosaccharides, which are often essential for full biological activity of natural alpha-peptides. In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexanecarboxylic acid (ACHC), both functionalized with a hydroxy group, to increase the solubility in water, and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a 'click reaction'. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.131

文献信息

• 2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic β-peptide conjugates
  作者：José J. Reina、Anna Bernardi

  DOI：10.1016/j.tet.2011.05.131

  日期：2011.8

  Oligomers of cyclic-beta-aminoacids possess a high resistance to peptidase-catalyzed hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These characteristics are attractive to develop new biologically active substances. However, cyclic-beta-peptides often show limited solubility in water and cannot be conjugated to biologically relevant fragments, such as oligosaccharides, which are often essential for full biological activity of natural alpha-peptides. In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexanecarboxylic acid (ACHC), both functionalized with a hydroxy group, to increase the solubility in water, and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a 'click reaction'. (C) 2011 Elsevier Ltd. All rights reserved.