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

Synthesis and characterization of a small library of bisglucosides: Influence of the nature of the diol/diphenol used in O-glucosylation. Carbohydr Res. 2020 Dec 05;:108217 Authors: Patry S, Robitzer M, Habas JP Abstract 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. PMID: 33317828 [PubMed - as supplied by publisher]
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Tags: Carbohydr Res Source Type: research