(R)-Phenyl-[((R)-tetrahydro-furan-2-carbonyl)-amino]-acetic acid methyl ester

• 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: (R)-Phenyl-[((R)-tetrahydro-furan-2-carbonyl)-amino]-acetic acid methyl ester
• 英文别名: methyl (2R)-2-[[(2R)-oxolane-2-carbonyl]amino]-2-phenylacetate
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: KCBGJJPTVXKVKK-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  左旋苯甘氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基吗啉 、 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 (R)-Phenyl-[((R)-tetrahydro-furan-2-carbonyl)-amino]-acetic acid methyl ester
  参考文献：
  名称：

  Rubrosides A−H, New Bioactive Tetramic Acid Glycosides from the Marine Sponge Siliquariaspongia japonica¹

  摘要：

  Eight new tetramic acid glycosides named rubrosides A-H have been isolated from the marine sponge Siliquariaspongia japonica. Their structures were elucidated on the basis of spectral data as tetramic acid glycosides containing polyenes terminating in a 4-chloro-2-methyltetrahydrofuran ring. The absolute stereochemistry of the furan functionality in the two major metabolites, rubrosides D and F, was determined by the NMR method using chiral anisotropic reagents for tetrahydro-2-furoic acid derived by RuO4 oxidation. The absolute stereochemistry of tetramic acid and of the sugar moieties in all rubrosides was deduced by chiral GC analysis of chemical degradation products. The rubrosides induced numerous large intracellular vacuoles in 3Y1 rat fibroblasts at concentrations of 0.5-1.0 mu g/mL, and rubrosides A, C, D, and E were cytotoxic against P388 murine leukemia cells with IC50 values of 0.046-0.21 mu g/mL. Most rubrosides show antifungal activity against Aspergillus fumigatus and Candida albicans.

  DOI：

  10.1021/jo981995v