methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate | 1321925-49-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate
• 英文别名: methyl (1S,2R,4R,5R)-4-(2-chloroethoxy)-5-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexane-1-carboxylate
• CAS: 1321925-49-8
• 化学式: C₁₅H₂₆ClNO₆
• 分子量: 351.828
• InChiKey: IHTQMQCWGPXBHM-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate 在 咪唑 、 sodium azide 、 碘 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 methyl (1S,2R,4R,5R)-4-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-5-(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：

  (1R)-6-methoxycarbonylcyclohex-3-ene-1-carboxylic acid 在 叠氮磷酸二苯酯 、 copper(II) bis(trifluoromethanesulfonate) 、 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 6.0h， 生成 methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-hydroxycyclohexanecarboxylate
  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