Methyl-D-glucofuranosid | 138052-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-D-glucofuranosid
• 英文别名: methyl D-glucofuranoside；methyl glucofuranosides；methyl α,β-D-glucofuranose；(2R,3R,4R)-2-[(1R)-1,2-dihydroxyethyl]-5-methoxyoxolane-3,4-diol
• CAS: 138052-46-7
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: ZSQBOIUCEISYSW-YDEIVXIUSA-N

物化性质

• 沸点：
  444.8±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl-D-glucofuranosid 以 环丁砜 为溶剂， 反应 0.5h， 以31.8%的产率得到1,6-脱水-Β-D-呋喃葡萄糖
  参考文献：
  名称：

  Synthesis, Characterization, and Lectin Recognition of Hyperbranched Polysaccharide Obtained from 1,6-Anhydro-d-hexofuranose

  摘要：

  1,6-Anhydro-D-hexofuranoses, such as 1,6-anhydro-beta-D-glucofuranose (1), 1,6-anhydro-beta-D-mannofuranose (2), and 1,6-anhydro-alpha-D-galactofuranose (3), were polymerized using a thermally induced cationic catalyst in dry propylene carbonate to afford hyperbranched polysaccharides (poly1-3) with degrees of branching from 0.40 to 0.46. The weight-average molecular weights of polyl - 3 measured by multiangle laser light scattering varied in the range from (1.02 to 5.84) x 10(4) g.mol(-1), which were significantly higher than those measured by size exclusion chromatography. The intrinsic viscosities ([eta]) of poly1 - 3 were very low in the range from 4.9 to 7.4 mL.g(-1). The exponent (alpha) in the Mark-Houkwink-Sakurada equation ([eta] = KM(alpha)) of the polymers was 0.20 to 0.33, which is < 0.5. The steady shear flow of poly1 - 3 in an aqueous solution exhibited a Newtonian behavior with steady shear viscosities independent of the shear rate. These viscosity characteristics were attributed to the spherical structures of hyperbranched polysaccharides in an aqueous solution. Poly1 - 3 contained a high portion of terminal units of 31-43 mol % nonreducing D-hexopyranosyl and D-hexofuranosyl units, in which the D-hexofuranosyl units were 20-44 mol %. Moreover, polyl and poly2 showed a strong interaction to Concanavalin A due to the cluster effect or multivalent effect of numerous nonreducing saccharide units on their surfaces with binding constants in the range from 1.7 x 10(4) to 2.7 x 10(5) M(-1).

  DOI：

  10.1021/bm2002413
• 作为产物：
  描述：

  甲醇 、 D-葡萄糖-二乙基缩硫醛 在 碘 作用下， 反应 32.0h， 以74%的产率得到Methyl-D-glucofuranosid
  参考文献：
  名称：

  裂解碳水化合物衍生物中乙缩醛和二硫缩醛的新方法

  摘要：

  用碘在甲醇中的稀溶液处理碳水化合物的乙缩醛和二硫代乙缩醛为裂解乙缩醛功能提供了一种简单，方便且高产的方法。

  DOI：

  10.1016/s0040-4039(00)83890-3

文献信息

• Transformation of Cellulose into Biodegradable Alkyl Glycosides by Following Two Different Chemical Routes
  作者：Nicolas Villandier、Avelino Corma

  DOI：10.1002/cssc.201000371

  日期：2011.4.18

  cellulose into long‐chain alkyl glycoside surfactants has been carried out following two different routes: (1) Direct transformation of cellulose to butyl‐, hexyl‐, octyl‐, decyl‐ and dodecyl‐α,β‐glycosides in an ionic liquid media and Amberlyst‐15Dry as catalysts, with mass yield of up to 82 %; and (2) two steps reaction with transformation of cellulose into methyl glucosides, with a procedure described

  纤维素向长链烷基糖苷表面活性剂的转化已通过以下两种不同的途径进行：（1）纤维素在离子性离子中直接转化为丁基，己基，辛基，癸基和十二烷基-β-糖苷。液体介质和Amberlyst-15Dry作为催化剂，质量产率高达82％；（2）两步反应，按照Zhang等人的描述，将纤维素转化为甲基葡糖苷，然后在Amberlyst-15Dry存在下，用1-辛醇和1-癸醇进行缩醛化。使用1-辛醇对纤维素进行直接转化的动力学研究表明，在费歇尔糖苷化过程中，纤维素的解聚反应仍在继续。由于醇的亲脂性的增加（其减少了与碳水化合物的接触），增加了醇的链长会降低总体反应速率。最后，测试了几种酸催化剂，使用Amberlyst-15Dry获得了最佳结果。
• Kinetic analysis of hexose conversion to methyl lactate by Sn-Beta: effects of substrate masking and of water
  作者：Irene Tosi、Anders Riisager、Esben Taarning、Pernille Rose Jensen、Sebastian Meier

  DOI：10.1039/c8cy00335a

  日期：——

  entry into the Sn-Beta-catalysed methyl lactate process using abundant hexose substrates. NMR spectroscopy is applied to show that the formation of methyl lactate occurs in two kinetic regimes for fructose, glucose and sucrose. The majority of methyl lactate is not formed from the substrate directly, but from methyl fructosides in a slow regime. At 160 °C, more than 40% of substrate carbon are masked (i

  简单的糖显示出有望用作在酒精溶剂中使用非均相催化剂形成燃料和化学物质的底物。Sn-Beta是特别适合将糖类裂解，异构化和脱水成更有价值的化学物质的催化剂。为了理解这些过程并通过优化它们来节省资源和时间，动力学和力学分析是有帮助的。在本文中，我们研究了使用大量己糖底物进入Sn-Beta催化的乳酸甲酯工艺的底物进入。应用NMR光谱法显示果糖乳酸的形成在果糖，葡萄糖和蔗糖的两个动力学机制中发生。乳酸甲酯的大部分不是直接由底物形成，而是由甲基果糖苷以缓慢的方式形成。在160°C下，超过40％的基材碳被掩盖了（即可逆保护原位）如使用水热合成的Sn-β时在几分钟内甲基果糖苷，而60％以上的甲基果糖苷可以在几分钟内用合成后处理的Sn-β产生。因此，在随后的果糖缓慢释放之前，大部分的底物被快速形成的甲基果糖苷所掩盖。该释放是Sn-β-催化的乳酸甲酯工艺中的限速步骤，但可以通过添加少量水来加速释放，但要以最大的乳酸甲酯产率为代价。
• Synthesis of methyl α- and β-maltosides
  作者：Norman W.H. Cheetham、Padmini Sirimanne

  DOI：10.1016/s0008-6215(00)84703-5

  日期：1981.10
• Miethchen, Ralf; Gabriel, Torsten, Chemische Berichte, 1993, vol. 126, # 10, p. 2309 - 2316
  作者：Miethchen, Ralf、Gabriel, Torsten

  DOI：——

  日期：——
• Interaction between methanol and d-glucose bis(benzeneboronate): synthesis of methyl d-glucofuranosides
  作者：June Briggs、Ian R. Mckinley、Helmut Weigel

  DOI：10.1016/s0008-6215(00)84874-0

  日期：1980.4