(4S,5R)-2-(dimethylamino)-5-methyl-Δ²-oxazoline-4-carboxylic acid | 246034-28-6

• 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: (4S,5R)-2-(dimethylamino)-5-methyl-Δ²-oxazoline-4-carboxylic acid
• 英文别名: (4S,5R)-2-dimethylamino-4-carboxy-5-methyl-Δ²-oxazoline；(4S,5R)-2-(dimethylamino)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylic acid
• CAS: 246034-28-6
• 化学式: C₇H₁₂N₂O₃
• 分子量: 172.184
• InChiKey: YPWIMYKXMIOLRU-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2-(dimethylamino)-5-methyl-Δ²-oxazoline-4-carboxylic acid 在 草酰氯 、 氨 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 109.0h， 生成 N-[2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranosyl]-(4S,5R)-2-dimethylamino-5-methyl-Δ²-oxazoline-4-carboxyamide
  参考文献：
  名称：

  Synthesis of N-Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2293::aid-ejoc2293>3.3.co;2-o
• 作为产物：
  描述：

  L-苏氨酸 、 ethyl (dimethylamino)formimidoate 以 甲醇 为溶剂， 反应 17.0h， 以59%的产率得到(4S,5R)-2-(dimethylamino)-5-methyl-Δ²-oxazoline-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of N-Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2293::aid-ejoc2293>3.3.co;2-o

文献信息

• SYNTHESIS AND CONFORMATIONAL ANALYSIS OF PSEUDOSUGAR ANALOGUES OF CHITOTRIOSE 1*
  作者：Gabriela Thiele、Antje Rottmann、Antje Germer、Erich Kleinpeter、Klaus-Dieter Spindler、Bjørnar Synstad、Vincent Eijsink、Martin Peter

  DOI：10.1081/car-120016847

  日期：——

  EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation afforded N,N"-diacetylpseudochitotriose 7. Coupling of 5 with heterocyclic or with Cbz protected aliphatic amino acids yielded glycosyl amides 8-12. Deprotection of 11 and 12 afforded the N,N'-diacetylpseudochitotriosyl amides of beta-alanine, 13, and L-arginine, 14. Molecular modelling calculations revealed that the pseudotrisaccharides exist in low energy extended conformations which show similar space filling as N,N',N"-triacetylchitotriose.
• Synthesis of N-Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors
  作者：Antje Rottmann、Bjørnar Synstad、Vincent Eijsink、Martin G. Peter

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2293::aid-ejoc2293>3.3.co;2-o

  日期：1999.9