methyl 2-S-acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-thio-α-D-mannopyranoside | 853943-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2-S-acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-thio-α-D-mannopyranoside
• 英文别名: methyl 2-thio-2-S-acetyl-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
• CAS: 853943-20-1
• 化学式: C₂₃H₂₆O₆S
• 分子量: 430.522
• InChiKey: WYFVNVWHODUQJI-AZZQQCEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2-S-acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-thio-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以77%的产率得到methyl 2-thio-3-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl 2-S-acetyl-3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015

文献信息

• Non-Glycosidically Linked Pseudodisaccharides: Thioethers, Sulfoxides, Sulfones, Ethers, Selenoethers, and Their Binding to Lectins
  作者：Ian Cumpstey、Clinton Ramstadius、Tashfeen Akhtar、Irwin J. Goldstein、Harry C. Winter

  DOI：10.1002/ejoc.200901481

  日期：2010.4

  Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such

  水解稳定的非糖苷连接的尾对尾假二糖通过远离组成单糖的异头中心的单个桥原子连接。发现一些具有硫桥或氧桥的此类假二糖在与香蕉凝集素和刀豆球蛋白 A 结合时充当二糖模拟物。描述了一种合成此类化合物的小型文库的通用途径。