(3R,3'S)-5-O-benzyl-3'-isobutyl-1,2-O-isopropylidenespiro[3-deoxy-α-D-erythro-pentofuranose-3,5'-piperazine]-2'-one | 1012796-13-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,3'S)-5-O-benzyl-3'-isobutyl-1,2-O-isopropylidenespiro[3-deoxy-α-D-erythro-pentofuranose-3,5'-piperazine]-2'-one
• CAS: 1012796-13-2
• 化学式: C₂₂H₃₂N₂O₅
• 分子量: 404.506
• InChiKey: LVNKQUNVPPLYMP-FIEIAYSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  78.05
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-3-{[(S)-1-(methoxycarbonyl)-3-methylbutyl]amino}-α-D-ribofuranose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到(3R,3'S)-5-O-benzyl-3'-isobutyl-1,2-O-isopropylidenespiro[3-deoxy-α-D-erythro-pentofuranose-3,5'-piperazine]-2'-one
  参考文献：
  名称：

  Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

  摘要：

  Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to alpha,alpha-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.038