methyl 2,3,4,6-tetra-O-allyl-β-D-glucopyranoside | 130791-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-allyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(prop-2-enoxy)-6-(prop-2-enoxymethyl)oxane
• CAS: 130791-20-7
• 化学式: C₁₉H₃₀O₆
• 分子量: 354.444
• InChiKey: BQYMBCRFFFNQFU-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-allyl-β-D-glucopyranoside 反应 56.0h， 生成 methyl 2,3,4,6-tetra-O-(9-amino-7-aza-4-thianon-6-onyl)-β-D-glucopyranoside
  参考文献：
  名称：

  On the Nature of the Multivalency Effect:  A Thermodynamic Model

  摘要：

  A quantitative model is proposed for the analysis of the thermodynamic parameters of multivalent interactions in dilute solutions or with immobilized multimeric receptor. The model takes into account all bound species and describes multivalent binding via two microscopic binding energies corresponding to inter- and intramolecular interactions (DeltaGdegrees(inter) and DeltaGdegrees(intra)), the relative contributions of which depend on the distribution of complexes with different numbers of occupied binding sites. The third component of the overall free energy, which we call the "avidity entropy" term, is a function of the degeneracy of bound states, Omega(i), which is calculated on the basis of the topology of interaction and the distribution of all bound species. This term grows rapidly with the number of receptor sites and ligand multivalency, it always favors binding, and explains why multivalency can overcome the loss of conformational entropy when ligands displayed at the ends of long tethers are bound. The microscopic parameters DeltaGdegrees(inter) and DeltadegreesG(intra) may be determined from the observed binding energies for a set of oligovalent ligands by nonlinear fitting with the theoretical model. Here binding data obtained from two series of oligovalent carbohydrate inhibitors for Shiga-like toxins were used to verify the theory. The decavalent and octavalent inhibitors exhibit subnanomolar activity and are the most active soluble inhibitors yet seen that block Shiga-like toxin binding to its native receptor. The theory developed here in conjunction with our protocol for the optimization of tether length provides a predictive approach to design and maximize the avidity of multivalent ligands.

  DOI：

  10.1021/ja038223n
• 作为产物：
  描述：

  碳酸丙烯乙酯 、 甲基 Β-D-吡喃葡萄糖苷 在 tris(dibenzylideneacetone)dipalladium (0) 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以95%的产率得到methyl 2,3,4,6-tetra-O-allyl-β-D-glucopyranoside
  参考文献：
  名称：

  Lakhmiri, Rajae; Lhoste, Paul; Sinou, Denis, Synthetic Communications, 1990, vol. 20, # 10, p. 1551 - 1554

  摘要：

  DOI：

文献信息

• LAKHMIRI, RAJAE;LHOSTE, PAUL;SINOU, DENIS, SYNTH. COMMUN., 20,(1990) N0, C. 1551-1554
  作者：LAKHMIRI, RAJAE、LHOSTE, PAUL、SINOU, DENIS

  DOI：——

  日期：——