O-(β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime

• 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: O-(β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime
• 英文别名: (2S,3R,4S,5R,6R)-2-[(E)-(2-diphenylphosphanylphenyl)methylideneamino]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₅H₂₆NO₆P
• 分子量: 467.458
• InChiKey: BMOUCWAMMGAYEH-OULQYYEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 O-(β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime 在 吡啶 作用下， 以62%的产率得到O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 148: Carbohydrate-derived oxime ethers stable towards hydrolysis—syntheses of ligands and complexes and a study of their catalytic properties

  摘要：

  The synthesis of new hydrolytically stable oxime ether ligands by condensation of various aldehydes with O-beta-D-glucopyranosylhydroxylamine 1 or O-beta-D-galactopyranosylhydroxylamine 4 is described. After peracetylation of the hydroxyl groups, ligands soluble in organic solvents were obtained. The ligands have been tested in transition metal-catalysed reactions. Phosphorus-containing ligands gave high yields in palladium-catalysed allylic alkylation and rhodium-catalysed hydrosilylation reactions although the enantioselectivities were low. A 1,3-diphenylallyl-palladium(II) complex of ligand 2b was prepared and its structure was established by X-ray diffraction analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00093-4
• 作为产物：
  描述：

  2-二苯基膦苯甲醛 、 O-(β-D-galactopyranosyl)hydroxylamine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到O-(β-D-galactopyranosyl)-2-diphenylphosphanylbenzaldoxime
  参考文献：
  名称：

  Enantioselective catalysis. Part 148: Carbohydrate-derived oxime ethers stable towards hydrolysis—syntheses of ligands and complexes and a study of their catalytic properties

  摘要：

  The synthesis of new hydrolytically stable oxime ether ligands by condensation of various aldehydes with O-beta-D-glucopyranosylhydroxylamine 1 or O-beta-D-galactopyranosylhydroxylamine 4 is described. After peracetylation of the hydroxyl groups, ligands soluble in organic solvents were obtained. The ligands have been tested in transition metal-catalysed reactions. Phosphorus-containing ligands gave high yields in palladium-catalysed allylic alkylation and rhodium-catalysed hydrosilylation reactions although the enantioselectivities were low. A 1,3-diphenylallyl-palladium(II) complex of ligand 2b was prepared and its structure was established by X-ray diffraction analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00093-4

文献信息

• Enantioselective catalysis. Part 148: Carbohydrate-derived oxime ethers stable towards hydrolysis—syntheses of ligands and complexes and a study of their catalytic properties
  作者：Henri Brunner、Maximilian Schönherr、Manfred Zabel

  DOI：10.1016/s0957-4166(03)00093-4

  日期：2003.5

  The synthesis of new hydrolytically stable oxime ether ligands by condensation of various aldehydes with O-beta-D-glucopyranosylhydroxylamine 1 or O-beta-D-galactopyranosylhydroxylamine 4 is described. After peracetylation of the hydroxyl groups, ligands soluble in organic solvents were obtained. The ligands have been tested in transition metal-catalysed reactions. Phosphorus-containing ligands gave high yields in palladium-catalysed allylic alkylation and rhodium-catalysed hydrosilylation reactions although the enantioselectivities were low. A 1,3-diphenylallyl-palladium(II) complex of ligand 2b was prepared and its structure was established by X-ray diffraction analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.