(2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-isopropyl-4-(trifluoromethanesulfonyloxy)-4,5-didehydro-piperidine | 848978-59-6

• 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: (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-isopropyl-4-(trifluoromethanesulfonyloxy)-4,5-didehydro-piperidine
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[(2S)-2-propan-2-yl-4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2H-pyridin-1-yl]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 848978-59-6
• 化学式: C₃₅H₅₆F₃NO₁₂S
• 分子量: 771.89
• InChiKey: WXTWVTDDNNYUQT-XCQFYCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-isopropyl-4-(trifluoromethanesulfonyloxy)-4,5-didehydro-piperidine 在 bis(triphenylphosphine)palladium(II)-chloride 盐酸 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 22.0h， 生成 2,3,4,6-tetra-O-pivaloyl-D-galactopyranose
  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：

  N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)isobutylideneamine 在 L-Selectride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-isopropyl-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