(1S,2R,4S,5R,11S)-1,2,5-trihydroxy-4-(hydroxymethyl)-11-methyl-3-oxa-7,10,13,16-tetraazaspiro[5.11]heptadecane-9,12,15-trione | 1012796-31-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (1S,2R,4S,5R,11S)-1,2,5-trihydroxy-4-(hydroxymethyl)-11-methyl-3-oxa-7,10,13,16-tetraazaspiro[5.11]heptadecane-9,12,15-trione
• 英文别名: (1S,2R,4S,5R,6R,11S)-1,4,5-trihydroxy-2-(hydroxymethyl)-11-methyl-3-oxa-7,10,13,16-tetrazaspiro[5.11]heptadecane-9,12,15-trione
• CAS: 1012796-31-4
• 化学式: C₁₄H₂₄N₄O₈
• 分子量: 376.367
• InChiKey: GBIQSXAZNBEMFR-WCQMCCFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (3'aR,5'S,6S,6'aR,11R)-5'-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2',2',6-trimethylspiro[1,4,7,10-tetrazacyclododecane-11,6'-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole]-2,5,8-trione 在 水 、 三氟乙酸 作用下， 反应 48.0h， 以94%的产率得到(1S,2R,4S,5R,11S)-1,2,5-trihydroxy-4-(hydroxymethyl)-11-methyl-3-oxa-7,10,13,16-tetraazaspiro[5.11]heptadecane-9,12,15-trione
  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