Hosoya Takashi, Kosma Paul, Rosenau Thomas
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Carbohydr Res. 2015 Jan 12;401:127-31. doi: 10.1016/j.carres.2014.10.013. Epub 2014 Oct 27.
The chemical nature of contact ion pairs and solvent-separated ion pairs from 2,3,4,6-tetra-O-methyl-α-D-mannopyranosyl triflate was investigated at the DFT(M06-2X) level of theory. Comparison of the present results to those obtained for the D-glucopyranosyl counterpart in our previous study indicated that the ion pairs from the D-mannopyranosyl triflate adopt B2,5-like conformations more preferably than those from the D-glucopyranosyl triflate. Similarly, 1,6-anhydro-D-mannopyranosyl dioxacarbenium ions bearing a (1)C4 conformation were shown to be more stable than the D-glucopyranosyl counterparts.
在密度泛函理论（DFT，M06 - 2X）水平下研究了2,3,4,6 - 四 - O - 甲基 - α - D - 甘露吡喃糖基三氟甲磺酸酯形成的接触离子对和溶剂分隔离子对的化学性质。将本研究结果与我们之前研究中D - 吡喃葡萄糖基对应物的结果进行比较表明，D - 甘露吡喃糖基三氟甲磺酸酯形成的离子对比D - 吡喃葡萄糖基三氟甲磺酸酯形成的离子对更倾向于采取类似B2,5的构象。同样，具有(1)C4构象的1,6 - 脱水 - D - 甘露吡喃糖基二氧杂碳鎓离子比D - 吡喃葡萄糖基对应物更稳定。
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