methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 178685-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• CAS: 178685-40-0
• 化学式: C₂₇H₃₄N₂O₁₄S
• 分子量: 642.638
• InChiKey: VEMQZKZHLNARQU-NFIQMXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  212.97
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.33h， 生成 methyl (S-D-biotinoyl-4-aminobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  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-Thiosialic acid methyl ester peracetate 、 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， 反应 2.5h， 以67%的产率得到methyl (S-4-nitrobenzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  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