Synthesis and characterization of a small library of bisglucosides: Influence of the nature of the diol/diphenol used in O-glucosylation

In this paper, the synthesis of different bisglucosides is investigated through the reaction of two acetylated glucose units with a diol (or diphenol) in order to develop a versatile molecular platform for the future development of bio-based polymers. A panel of five diols and one diphenol is initially used in order to examine the influence of their chemical skeleton on the reaction yield and both nature and proportion of formed species. Reaction products are identified using 1H and 13C NMR spectroscopies completed by MALDI-TOF MS technique. The nucleophilicity of these dihydroxy compounds is identified as being the main factor that governs the reaction characteristics. In particular, the best selectivity is obtained with the use of hydroquinone. Inversely, by-products (oligomers, deacetylated compounds) are observed with the diols defined by higher nucleophilicity despite the choice of stereoselective pathway using acyl protecting groups. [Display omitted] •A small library of bisglucosides was synthesized through O-glucosylation pathway.•It consists of the specific reaction of two glucose units with different diols or diphenol.•The nucleophilicity of dihydroxy compounds is the main factor that governs the reaction characteristics.•The best selectivity is observed with the use of hydroquinone.•Side reactions are observed with the diols characterized by higher nucleophilicities.