[2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester | 476371-45-6

• 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: [2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1S,2S,5R)-2-methoxy-5-(phenylmethoxymethyl)cyclopentyl]carbamate
• CAS: 476371-45-6
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: FYGIPDHLDBFERV-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl ester 在 10percent Pd/C jones reagent 、 甲酸铵 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 18.0h， 生成 2-tert-butoxycarbonylamino-3-methoxycyclopentanecarboxylic acid
  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：

  Toluene-4-sulfonic acid (1S,2R)-2-benzyloxymethyl-cyclopent-3-enyl ester 在 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 sodium azide 、 三氟化硼乙醚 、 四氯化钛 、 氯化铵 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 44.33h， 生成 [2-(benzyloxymethyl)-5-methoxycyclopentyl]carbamic acid tert-butyl 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

文献信息

• Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical β-Peptides That Fold in Water
  作者：Matthew G. Woll、John D. Fisk、Paul R. LePlae、Samuel H. Gellman

  DOI：10.1021/ja0258778

  日期：2002.10.1

  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.