2-deoxy-2-{[4-(diphenylphosphino)benzoyl]amino}-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-{[4-(diphenylphosphino)benzoyl]amino}-D-glucopyranose
• 英文别名: 4-diphenylphosphanyl-N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
• 化学式: C₂₅H₂₆NO₆P
• 分子量: 467.458
• InChiKey: KTUQZIXZJIDCMC-BBPVLXATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-二苯基膦苯甲酸 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， 反应 1.0h， 生成 2-deoxy-2-{[4-(diphenylphosphino)benzoyl]amino}-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

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.