Development of Selective Synthetic Reactions of Sugars Based on Their Complexation.

(1)糖的选择性合成反应的研究进展。经间苯二酚醛环四聚体氢键络合溶解于四氯化碳中的核糖经甲醇甲基化得到高度立体选择性的甲基倍萘酚呋喃苷。(2)通过氢键对糖的分子识别。间苯二酚-醛环四聚体在糖的氢键固定中发现了轻微的结构差异。因此可以区分果糖和葡萄糖，以及甲基葡萄糖苷的α异头和β异头。(3)基于诱导圆二色性的糖构象测定。间苯二酚-醛环四聚体的糖配合物表现出圆二色性，具有分裂棉效应。棉花效应的迹象可能与糖的构象有关，凋零C1或1C。(4)一类新型糖粘合剂的研制。以八杂环为基础制备了一类新的大环。它被8条长烷基链官能化，链上有极性OH基团。在氯仿中发现这个大环可以从水中提取包括糖在内的各种极性物质。不仅单糖（葡萄糖和果糖），双糖也可以用这种方法溶解。这项工作因此打开了一个全新的糖化学领域的大门，基于极性有机介质中特定的主客相互作用。这个概念可以应用于糖的合成、分析、结构和有机方面。

(1) Development of Selective Synthetic Reactions of Sugars.Ribose solubilized in carbon tetrachloride via hydrogen-bonding complexation with resorcinolaldehyde cyclotetramer was found to undergo methylation with methanol to give methyl betaribofuranoside highly stereoselectively.(2) Molecular Recognition of Sugars via Hydrogen-Bonding.Resorcinol-aldehyde cyclotetramer was found to discriminate slight structural differences in sugars in their hydrogen-bonding fixation. It was thus possible to differentiate fructose vs glucose and alpha anomer of methyl glucopyranoside from the beta anomer.(3) Determination of Sugar Conformation Based on Induced Circular Dichroism.The sugar complexes of resorcinol-aldehyde cyclotetramer exhibit circular dichroism with split Cotton effects. The signs of the Cotton effects could be correlated with the conformation of the sugar, wither C1 or 1C.(4) Development of a New Class of Sugar Binder.A new class of macrocycle based on an octaazamacrocycle was prepared. It was functionalized by eight long-alkyl chains having polar OH groups. This macrocycle in chloroform was found to extract various polar materials including sugars from water. Not only monosaccharides (glucose and fructose) but also disaccharides could be solubilized in this manner.This work thus opens the door to an entirely new field of sugar chemistry, based on apecific host-guest interactions in apolar organic media. This concept can be applied to the synthetic, analytical, structural, and organic aspects of the sugars.