S-(4-nitrobenzyl) 2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside | 325470-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-(4-nitrobenzyl) 2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• CAS: 325470-07-3
• 化学式: C₂₉H₃₇NO₁₇S
• 分子量: 703.675
• InChiKey: PHJFUKOWEJRIBT-IYXZENIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  242.79
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  S-(4-nitrobenzyl) 2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.0h， 生成 S-(4-aminobenzyl) methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid]oate-(2,6)-2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-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：

  S-(4-nitrobenzyl) 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到S-(4-nitrobenzyl) 2,3-di-O-acetyl-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-acetyl-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