Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

Guijun Wang,Hao Yang,Sherman Coleman,Sherwin Cheuk

doi:10.3762/bjoc.7.31

Abstract

Low molecular weight gelators are an important class of molecules. The supramolecular gels formed by carbohydrate derived low molecular weight gelators are interesting soft materials that show great potential for many applications. Previously, we have synthesized a series of methyl 4,6-O-benzylidene-α-D-glucopyranoside derivatives and found that several of them are good gelators for water, aqueous mixtures of DMSO, or aqueous mixtures of ethanol. The gelation efficiency of these glycolipid derivatives is dependent upon the structures of their acyl chains. In order to understand the influence of the anomeric position of the sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The synthesis and characterization of these novel analogs are reported.

Highlights

In recent years, the field of low molecular weight gelators (LMWGs) has received a great deal of attention
The structures of LMWGs span a diverse range; carbohydrates have frequently been used in the synthesis of LMWGs because they are naturally abundant and possess multiple chiral centers that can be selectively functionalized [15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37]
We have found that further derivatization of the glucose headgroup to form different glycolipids can result in organogelators [3437]

Summary

Introduction

The field of low molecular weight gelators (LMWGs) has received a great deal of attention. Several of these compounds proved to be effective gelators for organic solvents and aqueous solutions [34,35,36,37]. Monoesters with alkynyl groups containing 5–7 carbons (Figure 2, 5–7) are good gelators for water or aqueous ethanol mixtures. To further understand the structural influence of the anomeric position of the sugar headgroup on self-assembly, we synthesized analogs using head group 8 [38] (Figure 2), in which the anomeric methoxy group was replaced with a hydrogen atom and contained a similar series of acyl chains to those in compounds 2–4.

Results

Conclusion