benzyl N-[2-oxo-5-(2-oxo-2-phenylethyl)-5,6-dihydro-2H-3-pyranyl]carbamate | 1019654-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl N-[2-oxo-5-(2-oxo-2-phenylethyl)-5,6-dihydro-2H-3-pyranyl]carbamate
• CAS: 1019654-17-1
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: KEQBAMZYWWVSOE-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  (RS)-methyl 2-[(1RS,2SR,3SR)-2-benzoyl-3-({[(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)cyclopropyl]-2-{[(benzyloxy)carbonyl]amino}ethanoate 在 四丁基氟化铵 作用下， 以37%的产率得到benzyl N-[2-oxo-5-(2-oxo-2-phenylethyl)-5,6-dihydro-2H-3-pyranyl]carbamate
  参考文献：
  名称：

  A Concise Route to β-Cyclopropyl Amino Acids Utilizing 1,2-Dioxines and Stabilized Phosphonate Nucleophiles

  摘要：

  1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give beta-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer-Villiger conditions. Standard deprotection protocols produced a series of known beta-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.

  DOI：

  10.1021/jo7024256