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

基于糖的络合选择性合成反应的发展。

基本信息

批准号：
01470094
负责人：
AOYAMA Yasuhiro
金额：
$ 4.29万
依托单位：
Nagaoka University of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (B)
财政年份：
1989
资助国家：
日本
起止时间：
1989 至 1990
项目状态：
已结题

项目摘要

(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.

（1）开发糖的选择性合成反应。ribose通过氢键在四氯化碳中溶于氢 - 甲醇环甲甲基甲醇与甲醇的甲基化相结合，从而提供甲基甲醇，从而提供甲基甲苯甲甲基的甲基甲醇。发现环转聚合物可以区分其氢键固定中糖的轻微结构差异。因此，有可能区分甲基葡萄糖糖苷的果糖与葡萄糖和α厌氧剂与β疾病剂。（3）基于诱导的圆形二分法的确定糖构象。溶质醇 - 醛醛环糖甲的糖络合物具有圆形二色剂具有圆形二色性，表现出具有分裂棉花效应的圆形二分法。棉效应的迹象可能与糖的构象相关，枯萎的C1或1C。（4）开发了新的糖粘合剂。制定了基于八叶芳族小环的新的大环。它通过具有极地OH基团的八个长烷基链功能化。发现该大环在氯仿中提取各种极性材料，包括水中的糖。不仅单糖（葡萄糖和果糖），而且可以以这种方式溶解二糖。因此，这项工作为基于Apolar Organic Media中的Apoltific Host-Guest相互作用打开了全新的糖化学领域。该概念可以应用于糖的合成，分析，结构和有机方面。