Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(4-diphenylphosphanyl-benzoylamino)-tetrahydro-pyran-4-yl ester | 497096-73-8

• 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: Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(4-diphenylphosphanyl-benzoylamino)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[(4-diphenylphosphanylbenzoyl)amino]oxan-2-yl]methyl acetate
• CAS: 497096-73-8
• 化学式: C₃₃H₃₄NO₁₀P
• 分子量: 635.607
• InChiKey: ATRYKWMNRHZXNN-FXSJFDGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：

  Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(4-diphenylphosphanyl-benzoylamino)-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以88%的产率得到2-deoxy-2-{[4-(diphenylphosphino)benzoyl]amino}-D-glucopyranose
  参考文献：
  名称：

  Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)01749-5
• 作为产物：
  描述：

  4-二苯基膦苯甲酸 、 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Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(4-diphenylphosphanyl-benzoylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)01749-5

文献信息

• Palladium-catalyzed Suzuki cross-coupling of aryl halides with aryl boronic acids in the presence of glucosamine-based phosphines
  作者：Robert Kolodziuk、Alexandra Penciu、Mustapha Tollabi、Eric Framery、Catherine Goux-Henry、Alexander Iourtchenko、Denis Sinou

  DOI：10.1016/s0022-328x(03)00636-3

  日期：2003.12

  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.