S-(4-nitrobenzyl) 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside | 51450-12-5

• 分子结构分类: 有机化合物
• 英文名称: S-(4-nitrobenzyl) 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: p-Nitrobenzyl-2-acetamido-3,4-6-tri-O-acetyl-1-thio-2-deoxy-β-D-glucopyranosid
• CAS: 51450-12-5
• 化学式: C₂₁H₂₆N₂O₁₀S
• 分子量: 498.511
• InChiKey: RAKNRIRXZCWHFU-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  160.37
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  S-(4-nitrobenzyl) 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以60%的产率得到S-(4-aminobenzyl) 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins

  摘要：

  The intimate involvement of carbohydrate-protein interactions in a number of important biological processes has prompted several research efforts towards developing new met:hods of investigating these glycobiological interactions. Biotinylated oligosaccharides are emerging as a new and powerful tool in this area of research, primarily due to their high affinity towards streptavidin and their ease of immobilization on matrices. Here we describe a novel synthetic approach towards biotinylated saccharides which incorporate a UV absorbing group into the final compounds. The synthetic strategy described is applicable to a variety of saccharides, with examples of biotinylated mono-, di-, and trisaccharides being prepared with overall high efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00201-7
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranose 、 对硝基溴化苄 在 乙酸肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到S-(4-nitrobenzyl) 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins

  摘要：

  The intimate involvement of carbohydrate-protein interactions in a number of important biological processes has prompted several research efforts towards developing new met:hods of investigating these glycobiological interactions. Biotinylated oligosaccharides are emerging as a new and powerful tool in this area of research, primarily due to their high affinity towards streptavidin and their ease of immobilization on matrices. Here we describe a novel synthetic approach towards biotinylated saccharides which incorporate a UV absorbing group into the final compounds. The synthetic strategy described is applicable to a variety of saccharides, with examples of biotinylated mono-, di-, and trisaccharides being prepared with overall high efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00201-7