1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-β-D-glucopyranose | 497096-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[(2-diphenylphosphanylbenzoyl)amino]oxan-2-yl]methyl acetate
• CAS: 497096-71-6
• 化学式: C₃₃H₃₄NO₁₀P
• 分子量: 635.607
• InChiKey: ZDKSETAWPRAYNN-GJQHGMRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-β-D-glucopyranose 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-D-glucopyranose
  参考文献：
  名称：

  Palladium-catalyzed asymmetric allylic alkylation using chiral glucosamine-based monophosphines

  摘要：

  An easy access to a new chiral phosphine-amide derived from D-glucosamine is described. Palladium-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with various carbon and amino nucleophiles in the presence of this ligand has been successfully carried out, enantiomeric excesses of up to 97% being obtained. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.015
• 作为产物：
  描述：

  2-二苯基膦苯甲酸 、 tetra-acetyl glucosamine 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以68%的产率得到1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-β-D-glucopyranose
  参考文献：
  名称：

  Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines

  摘要：

  Carbohydrate-substituted phosphines are easily obtained in quite good yields by coupling of protected or non-protected D-glucosamine with the corresponding diphenylphosphino acid. These neutral ligands, in association with palladium acetate, are very active catalysts in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines. The process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers, up to 97 000 are observed. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00636-3
• 作为试剂：
  描述：

  (±)-反式-1,3-二苯基烯丙基乙酸酯 、 苄胺 在 N,O-双三甲硅基乙酰胺 、 potassium acetate 、 Di-μ-chlorodiallylpalladium 、 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[2-(diphenylphosphino)benzoyl]amino}-β-D-glucopyranose 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 (-)-(R,E)-N-benzyl-(1,3-diphenyl-2-propenyl)amine 、 (E)-N-benzyl-1,3-diphenylprop-2-en-1-amine
  参考文献：
  名称：

  Palladium-Catalyzed Asymmetric Allylic Alkylation Using Phosphine-Amide Derived from Chiral trans-2-Aminocyclohexanol

  摘要：

  A novel phosphine-amide derived from resolved trans-2-aminocyclohexanol has been synthesized and studied in palladium-catalyzed asymmetric allylic alkylation of racemic (E)-1,3-diphenyl-2-propenyl acetate with various nucleophiles.

  DOI：

  10.1080/10426500902737372

文献信息

• Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water
  作者：Sophie Parisot、Robert Kolodziuk、Catherine Goux-Henry、Alexander Iourtchenko、Denis Sinou

  DOI：10.1016/s0040-4039(02)01749-5

  日期：2002.10

  Coupling of protected or non-protected D-glucosamine with o- or p-(diphenylphosphino)benzoic acid generates carbohydrate-substituted phosphines in quite good yields. The catalytic performance of these new neutral ligands is demonstrated in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines, and the process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers are observed, and the catalyst can be recycled. (C) 2002 Elsevier Science Ltd. All rights reserved.