((2R,4S,5S)-5-Amino-4-hydroxy-tetrahydro-pyran-2-yl)-acetic acid | 138093-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: ((2R,4S,5S)-5-Amino-4-hydroxy-tetrahydro-pyran-2-yl)-acetic acid
• 英文别名: 2-[(2R,4S,5S)-5-amino-4-hydroxyoxan-2-yl]acetic acid
• CAS: 138093-94-4
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: JSZGDHVDTZZWMK-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (-)-galantinic acid 在 盐酸 作用下， 反应 14.0h， 生成 (+)-galantinic acid 、 ((2R,4S,5S)-5-Amino-4-hydroxy-tetrahydro-pyran-2-yl)-acetic acid
  参考文献：
  名称：

  Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid

  摘要：

  The proposed structure of galantin 1, a peptide antibiotic isolated from Bacillus pulvifaciens as a mixture of congeners (1a with the D-ornithine residue and lb with D-lysine; 1a/1b = 9/1), was shown to be incorrect by total synthesis. The substructure 3a, named galantinic acid, was an artifact, and its correct structure was assumed to be the hydroxylated form, 20a or 20b, by spectroscopic comparisons of synthetic la with natural galantin I. The synthesis of both diastereomers, 4a and 4b, again suggested that the sequence of the spermidine moiety of galantin I should be N5,N8. Finally, the correct structure of galantin I as 5a was confirmed by the synthesis of diastereomers 5a and 5b. The synthesis of 5a was accomplished in a convergent manner by the coupling of the protected forms of the constituent amino acids: D-ornithine, 6b, D-alanine, 23b, 11b, 8c, and 19a. Galantinic acid residue 20a, present in natural galantin 1, was found to undergo cyclization with retention of its C3 configuration under the chemical degradation conditions to give the artifact 3a. In order to elucidate the mode of cyclization of 20a to 3a, the synthesis of 20a and its analogues was accomplished in a stereoselective manner from D-serine. The synthesis was characterized by the stereoselective epoxidation of hydroxymethyl (Z)-allylamine 34 and alpha,beta-unsaturated delta-lactone 39. Acidolysis of 20a, 20b, and their analogues suggested that the stereoselective cyclization of galantinic acid was initiated by the formation of delta-lactone 54, which through the sequence of reactions should afford the artifact 3a.

  DOI：

  10.1021/ja00029a031