(2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-5,6-didehydro-piperidin-4-one

• 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: (2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-5,6-didehydro-piperidin-4-one
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R)-2-[(2-bromophenyl)methyl]-4-oxo-2,3-dihydropyridin-1-yl]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₃₈H₅₄BrNO₁₀
• 分子量: 764.751
• InChiKey: LUIMOVHOWBNDQS-JAMMDLCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-5,6-didehydro-piperidin-4-one 、 N-苯基双(三氟甲烷磺酰)亚胺 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到(2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-4-(trifluoromethanesulfonyloxy)-4,5-didehydro-piperidine
  参考文献：
  名称：

  Palladium-catalysed C–C coupling reactions in the enantioselective synthesis of 2,4-disubstituted 4,5-dehydropiperidines using galactosylamine as a stereodifferentiating auxiliary

  摘要：

  Stereoselective synthesis of enantiomerically pure 2,4-disubstituted piperidine derivatives, which are considered interesting pharmacophoric structures, was achieved starting with a tandem Mannich-Michael reaction sequence on O-pivaloylated N-galactosyl aldimines. Subsequent conversion of the thus formed 2-substituted dehydropiperidinones into the corresponding enol tri-flates was carried out by conjugate hydride addition and trapping the enolate with N,N-bis(trifluoromethanesulfonyl)aniline. Their Suzuki-Miyaura coupling with aryl and heteroaryl boronic acids was performed under, conditions compatible with the carbohydrate structure, in particular, with the sensitive N-glycosidic bond. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.074
• 作为产物：
  描述：

  、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 zinc(II) chloride 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-5,6-didehydro-piperidin-4-one 、 (2R)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(2-bromobenzyl)-5,6-didehydro-piperidin-4-one
  参考文献：
  名称：

  立体选择性合成苯并吗啡酮衍生物，其中过环戊基化的半乳糖为手性助剂。

  摘要：

  DOI：

  10.1002/anie.200504090