(S)-4-((2S,4S)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 130914-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-4-((2S,4S)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(2S,4S)-4-hydroxy-6-oxooxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 130914-19-1
• 化学式: C₁₅H₂₅NO₆
• 分子量: 315.367
• InChiKey: WTGQBCBGVLFXBH-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,5S,4'S)-5-<3-N-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl>-3-hydroxy-5-pentanolide 、 (S)-4-((2S,4S)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 、 叔丁基二甲硅基三氟甲磺酸酯 生成 (S)-4-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  SAKAI, NAOMI;OHFUNE, YASUFUMI, TETRAHEDRON LETT., 31,(1990) N9, C. 4151-4154

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-4-((2R,3R)-3-Formyl-oxiranyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 苄基三甲基氢氧化铵 叔丁基过氧化氢 、 ammonia borane 、 苯硒酚 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium phenylseleno(triethyl)borate 、 三氟乙酸酐 、 柠檬酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 异丙醇 、 苯 为溶剂， 反应 76.75h， 生成 (S)-4-((2S,4S)-4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  高效合成（-）-没食子酸的修饰结构。

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)97567-1

文献信息

• Total synthesis of galantin I. Acid-catalyzed cyclization of galantinic acid
  作者：Naomi Sakai、Yasufumi Ohfune

  DOI：10.1021/ja00029a031

  日期：1992.1

  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.