2-azidoethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 870136-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-(2-azidoethoxy)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 870136-62-2
• 化学式: C₆₃H₅₃N₃O₁₈
• 分子量: 1140.12
• InChiKey: FLZVBRYEBVWDOR-OITHESAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  84
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  2-azidoethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以91%的产率得到2-azidoethyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120

  摘要：

  Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl beta-D-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA(120) was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human alpha 1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.036
• 作为产物：
  描述：

  2-chloroethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 sodium azide 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以90%的产率得到2-azidoethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120

  摘要：

  Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl beta-D-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA(120) was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human alpha 1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.036