2-chloroethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 870136-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloroethyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 870136-61-1
• 化学式: C₆₃H₅₃ClO₁₈
• 分子量: 1133.56
• InChiKey: LLCXMRNZXIUPCB-OITHESAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.92
• 重原子数：
  82.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  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 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 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：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl bromide 、 2-氯乙醇 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2-chloroethyl (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