(5S,6R)-1-allyl-5-(benzyloxy)-6-methylpiperidin-2-one | 1200404-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5S,6R)-1-allyl-5-(benzyloxy)-6-methylpiperidin-2-one
• 英文别名: (5S,6R)-6-methyl-5-phenylmethoxy-1-prop-2-enylpiperidin-2-one
• CAS: 1200404-68-7
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: LIHIJKZQMKOYCH-HIFRSBDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6R)-1-allyl-5-(benzyloxy)-6-methylpiperidin-2-one 在 rhodium trichloride hydrate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以88%的产率得到(5S,6R)-5-(benzyloxy)-6-methylpiperidin-2-one
  参考文献：
  名称：

  Asymmetric syntheses of 6-deoxyfagomin, d-deoxyrhamnojirimycin, and d-rhamnono-1,5-lactam

  摘要：

  N-Allyl protected 3-O-benzyloxglutarimide 11 was synthesized as a useful variant of the chiral building block 10. This modification allowed a high-yielding deprotection of the allyl group from the lactam intermediate 14. Starting from this building block, the asymmetric syntheses of aza-sugars 6-deoxyfagomine (2), D-rhamnono-1,5-lactam (6), as well as D-deoxyrhamnojirimycin (5) have been achieved in high regio- and/or diastereo-controlled manner. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.083
• 作为产物：
  描述：

  (5S)-1-allyl-5-(benzyloxy)-6-hydroxy-6-methylpiperidin-2-one 在 三乙基硅烷 、 三氟化硼乙醚 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以91%的产率得到(5S,6R)-1-allyl-5-(benzyloxy)-6-methylpiperidin-2-one
  参考文献：
  名称：

  Asymmetric syntheses of 6-deoxyfagomin, d-deoxyrhamnojirimycin, and d-rhamnono-1,5-lactam

  摘要：

  N-Allyl protected 3-O-benzyloxglutarimide 11 was synthesized as a useful variant of the chiral building block 10. This modification allowed a high-yielding deprotection of the allyl group from the lactam intermediate 14. Starting from this building block, the asymmetric syntheses of aza-sugars 6-deoxyfagomine (2), D-rhamnono-1,5-lactam (6), as well as D-deoxyrhamnojirimycin (5) have been achieved in high regio- and/or diastereo-controlled manner. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.083

文献信息

• Asymmetric syntheses of 6-deoxyfagomin, d-deoxyrhamnojirimycin, and d-rhamnono-1,5-lactam
  作者：Rui Fu、Yu Du、Zhao-Ying Li、Wei-Xuan Xu、Pei-Qiang Huang

  DOI：10.1016/j.tet.2009.09.083

  日期：2009.11

  N-Allyl protected 3-O-benzyloxglutarimide 11 was synthesized as a useful variant of the chiral building block 10. This modification allowed a high-yielding deprotection of the allyl group from the lactam intermediate 14. Starting from this building block, the asymmetric syntheses of aza-sugars 6-deoxyfagomine (2), D-rhamnono-1,5-lactam (6), as well as D-deoxyrhamnojirimycin (5) have been achieved in high regio- and/or diastereo-controlled manner. (C) 2009 Elsevier Ltd. All rights reserved.