(1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester | 476371-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester
• CAS: 476371-58-1
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: QBXRADSFWPBAGR-KIVGGJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester 在 硼烷四氢呋喃络合物 、 18-冠醚-6 、 氨 、 sodium 、 碳酸氢钠 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 47.5h， 生成 [(1R,2R,5R)-2-(tert-Butoxycarbonylamino-methyl)-5-hydroxymethyl-cyclopentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778
• 作为产物：
  描述：

  苄基氯甲基醚 在 吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 sodium azide 、 四氯化钛 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 116.5h， 生成 (1S,2R,5R)-2-Benzyloxymethyl-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water

  摘要：

  A stereoselective synthetic route is reported for the introduction of side chains at the 3-position of trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPC precursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed of the 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstituted analogues, as shown by their similar circular dichroism signatures. The added diversity of the new residues provides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selected hexamer in aqueous solution. The NOES between protons on nonadjacent residues are characteristic of the 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometrically defined fashion, which should facilitate the design of beta-peptides for biological applications.

  DOI：

  10.1021/ja0258778