tert-butyl (1S,4R,5R,6S)-5-(benzyloxy)-4-methyl-2-oxo-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate | 1200404-72-3

• 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: tert-butyl (1S,4R,5R,6S)-5-(benzyloxy)-4-methyl-2-oxo-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• 英文别名: tert-butyl (1S,4R,5R,6S)-4-methyl-2-oxo-5-phenylmethoxy-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• CAS: 1200404-72-3
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: CLPVJEHHZCGGCW-RZFFKMDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,4R,5R,6S)-5-(benzyloxy)-4-methyl-2-oxo-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate 在 samarium diiodide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以80%的产率得到tert-butyl (2R,3R,4R)-3-(benzyloxy)-4-hydroxy-2-methyl-6-oxopiperidine-1-carboxylate
  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：

  tert-butyl (5S,6R)-5-(benzyloxy)-6-methyl-2-oxo-5,6-dihydropyridine-1(2H)-carboxylate 在 叔丁基过氧化氢 、 potassium carbonate 、 四丁基氟化铵 作用下， 以 正壬烷 、 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到tert-butyl (1S,4R,5R,6S)-5-(benzyloxy)-4-methyl-2-oxo-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
  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