3-epi-galantinic acid | 130914-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 3-epi-galantinic acid
• 英文别名: (3R,5S,6S)-6-amino-3,5,7-trihydroxyheptanoic acid
• CAS: 130914-23-7
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: ISCLAUVNBIFWBC-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3R,5S,4'S)-5-<3-N-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-3-hydroxy-5-pentanolide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以82%的产率得到3-epi-galantinic 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

文献信息

• Efficient synthesis of the revised structure of (−)-galantinic acid.
  作者：Naomi Sakai、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(00)97567-1

  日期：——

  The synthesis of the revised structure of galantinic acid was accomplished starting from the serinal derivative 4 via a stereoselective epoxidation of hydroxymethyl-Z-allyl amine 5 and δ-substituted-α, β-unsaturated-δ-lactone 9.

  galantinic酸的修改后的结构的合成完成从serinal衍生物开始4经由羟甲基的立体选择性环氧化ž -烯丙基胺5和δ -substituted- α，β -unsaturated- δ -内酯9。
• SAKAI, NAOMI;OHFUNE, YASUFUMI, TETRAHEDRON LETT., 31,(1990) N9, C. 4151-4154
  作者：SAKAI, NAOMI、OHFUNE, YASUFUMI

  DOI：——

  日期：——
• IKOTA, NOBUO, HETEROCYCLES, 32,(1991) N, C. 521-528
  作者：IKOTA, NOBUO

  DOI：——

  日期：——
• Synthesis of (—)-Galantinic Acid from D-Ribonolactone
  作者：Nobuo Ikota

  DOI：10.3987/com-91-5669

  日期：——

  The synthesis of the revised structure of (-)-galantinic acid was achieved from D-ribonolactone.