(4S,5R)-N-benzyloxycarbonyl-4-benzyl-5-propionyl-1,3-oxazinan-6-one | 1444199-19-2

• 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)-N-benzyloxycarbonyl-4-benzyl-5-propionyl-1,3-oxazinan-6-one
• CAS: 1444199-19-2
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: URBIUXMBXWGSFS-AZUAARDMSA-N

反应信息

• 作为反应物：
  描述：

  (4S,5R)-N-benzyloxycarbonyl-4-benzyl-5-propionyl-1,3-oxazinan-6-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以85%的产率得到
  参考文献：
  名称：

  Synthesis of N-Cbz-Substituted β3-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones

  摘要：

  Stereoselective synthesis of N-Cbz-substituted beta-amino ketones exploiting the versatile 1,3-oxazin-6-one scaffold is reported. The 4-substituted 1,3-oxazinan-6-ones were enolized and acylated diastereoselectively by addition of various acyl halides. Acidic decarboxylation was then employed to smoothly transform the 5-acylated products to chiral beta-amino ketones. This methodology further highlights the utility of the 1,3-oxazinan-6-one as a scaffold to access valuable synthons that are used in the peptidomimetic field.

  DOI：

  10.1055/s-0032-1318345
• 作为产物：
  描述：

  、 丙酰氯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到(4S,5R)-N-benzyloxycarbonyl-4-benzyl-5-propionyl-1,3-oxazinan-6-one
  参考文献：
  名称：

  Synthesis of N-Cbz-Substituted β3-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones

  摘要：

  Stereoselective synthesis of N-Cbz-substituted beta-amino ketones exploiting the versatile 1,3-oxazin-6-one scaffold is reported. The 4-substituted 1,3-oxazinan-6-ones were enolized and acylated diastereoselectively by addition of various acyl halides. Acidic decarboxylation was then employed to smoothly transform the 5-acylated products to chiral beta-amino ketones. This methodology further highlights the utility of the 1,3-oxazinan-6-one as a scaffold to access valuable synthons that are used in the peptidomimetic field.

  DOI：

  10.1055/s-0032-1318345