(2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)-4-(5-pyrimidyl)-4,5-didehydro-piperidine | 848978-72-3

• 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-(3-pyridyl)-4-(5-pyrimidyl)-4,5-didehydro-piperidine
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[(2S)-2-pyridin-3-yl-4-pyrimidin-5-yl-3,6-dihydro-2H-pyridin-1-yl]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 848978-72-3
• 化学式: C₄₀H₅₆N₄O₉
• 分子量: 736.906
• InChiKey: WMGCOHZHXHEMHH-BUOONKCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)-4-(5-pyrimidyl)-4,5-didehydro-piperidine 在 盐酸 作用下， 以 甲醇 为溶剂， 以91%的产率得到(2S)-2-(3-pyridyl)-4-(5-pyrimidyl)-4,5-didehydropiperidine
  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：

  2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-tetrahydro-pyran-4-yl ester 在 bis(triphenylphosphine)palladium(II)-chloride L-Selectride 、 caesium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 (2S)-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)-4-(5-pyrimidyl)-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

文献信息

• Palladium-catalysed C–C coupling reactions in the enantioselective synthesis of 2,4-disubstituted 4,5-dehydropiperidines using galactosylamine as a stereodifferentiating auxiliary
  作者：Stephan Knauer、Horst Kunz

  DOI：10.1016/j.tetasy.2004.11.074

  日期：2005.1

  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.