methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate | 1321925-52-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate
• CAS: 1321925-52-3
• 化学式: C₂₁H₄₀ClNO₆Si
• 分子量: 466.09
• InChiKey: KQTMDTKOEJTNSV-YLFCFFPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.09
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-5-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate 在 sodium azide 、 碘 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以100%的产率得到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：

  在 咪唑 、 盐酸 、 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 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 methyl (1S,2R,4R,5R)-2-(tert-butoxycarbonylamino)-4-(2-chloroethoxy)-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