methyl (2S)-1-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]-2-pyrrolidinecarboxylate | 436843-94-6

• 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: methyl (2S)-1-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]-2-pyrrolidinecarboxylate
• 英文别名: methyl (2S)-1-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]pyrrolidine-2-carboxylate
• CAS: 436843-94-6
• 化学式: C₁₆H₁₇BrN₂O₃
• 分子量: 365.227
• InChiKey: AKXSNGGBAZLBLA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-1-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]-2-pyrrolidinecarboxylate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以76%的产率得到(8aS)-2-phenyl-6,7,8,8a-tetrahydro[1,3]oxazolo[4,5-f]indolizin-9(4H)-one
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z
• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 、 L-脯氨酸甲酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以82%的产率得到methyl (2S)-1-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z