methyl 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside | 221690-32-0

• 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 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside
• 英文别名: (2R,4aR,6S,7R,8S,8aR)-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 221690-32-0
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: AXBXPTIJUIPASI-DBHDPKECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到methyl 2,3-di-O-methyl-4-O-p-methoxybenzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies

  摘要：

  In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor anti-bacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.018
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 methyl 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies

  摘要：

  In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor anti-bacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.018

文献信息

• Synthesis of Conformationally-Locked <i><i>cis</i></i>- and <i><i>trans</i></i>-Bicyclo[4.4.0] Mono-, Di-, and Trioxadecane Modifications of Galacto- and Glucopyranose; Experimental Limiting ³<i>J</i>_H,H Coupling Constants for the Estimation of Carbohydrate Side Chain Populations and Beyond
  作者：Harsha Amarasekara、Suresh Dharuman、Takayuki Kato、David Crich

  DOI：10.1021/acs.joc.7b02891

  日期：2018.1.19

  proportions can be determined from the three sets of ideal limiting 3JH5,H6R and 3JH5,H6S coupling constants in combination with the time-averaged experimental coupling constants. Literature values for the limiting coupling constants, obtained by the study of model compounds, the use of the Haasnoot–Altona and related equations, or quantum mechanical computations, can result in computed negative populations

  六吡喃糖侧链组成三个交错的构象，其比例可以从三组理想的限制性3 J H5，H6R和3 J H5，H6S耦合常数与时间平均实验耦合常数结合确定。通过模型化合物的研究，使用Haasnoot–Altona和相关方程式或进行量子力学计算而获得的极限耦合常数的文献值，可以得出三个理想构型之一的负种群。这样的值是由于极限耦合常数的误差和/或非理想构象异构体的数量引起的。我们描述了一系列顺式-和的合成和分析反式稠合的单，双和三氧杂双环[4.4.0]辛烷样化合物。从内部模型（-CH（OR）-CH（OR）-）到终端系统（-CH（OR）-CH 2（OR））的数据应用的校正因子是通过与其他模型进行比较得出的，并在以下情况下应用必要的。如此得出的极限偶联常数应用于三种模型吡喃吡喃糖苷的侧链构象，从而得出计算的构象异构体数没有负值。尽管主要是为六吡喃糖侧链开发的，但具有给出的校正因子，有限的偶联常数适用于更高级的碳