(5S,6S)-5-benzyloxy-6-(n-hexadecyl)-1-(4-methoxybenzyl)-2-piperidinone | 1160427-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,6S)-5-benzyloxy-6-(n-hexadecyl)-1-(4-methoxybenzyl)-2-piperidinone
• CAS: 1160427-52-0
• 化学式: C₃₆H₅₅NO₃
• 分子量: 549.838
• InChiKey: HCOXWURAUDSNTN-PXLJZGITSA-N

反应信息

• 作为产物：
  描述：

  在 六甲基磷酰三胺 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 (5S,6S)-5-benzyloxy-6-(n-hexadecyl)-1-(4-methoxybenzyl)-2-piperidinone
  参考文献：
  名称：

  Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones

  摘要：

  Chemo- and diastereoselective transformation of the N,O-acetals and their chain tautomers (4/5), readily derived from protected 3-hydroxyglutamide 1a, Was Studied. It Was Uncovered that while the reaction with a combination of boron trifluoride etherate/zinc borohydride led to cyclic products (5S,6S/R)-6-alkyl-5-benzyloxy-2-piperidinones 3/2, and 6 in modest chemo- and diastereoselectivities, the reaction of 4/5 with zinc borohydride led exclusively to the formation of the ring-opening products 6 in excellent anti-diastereoselectivities. On the basis of the latter reaction, a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones 3 was disclosed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.021