Easy access to a carbohydrate-based template for stimuli-responsive surfactants

Abstract

In this paper we describe the synthesis of a new carbohydrate-based building block functionalized with azido or amino groups on the 2 and 4 positions. The building block can be synthesized in anomerically pure form in only five scalable steps starting from commercially available levoglucosan. It was shown that the building block could undergo alkylations under strongly basic conditions. The building block with azido groups could furthermore take part in CuAAC reactions, generating derivatives with ester or carboxylic acid functionalities. In addition, the anomeric mixture of the building block was used for the synthesis of a molecule that could act as an emulsifier only in the presence of Zn2+ ions.

Ring-System-Based Conformational Switches and their Applications in Sensing and Liposomal Drug Delivery

“…64,65 This concept was further developed into novel sugar-based surfactants possessing two amino groups at the 2-and 4-positions, which were then used to chelate with metal Unexpectedly, compounds 48-50 did not change the conformation from 4 C 1 to 1 C 4 under the influence of metal ions. 66 The reason for this might be that these three amine derivatives cannot easily adopt the 1 C 4 conformation due to a steric clash between the methylene group at C5 and the anomeric substituents, when adopting the axial-rich conformation. However, when using the picoloyl group at 3-O and 6-O in D-glucopyranose (51), with the -configuration, the anomeric substituent becomes equatorial upon the conformational flip.…”