Expanding the Scope of -Glycoside Synthesis from Unstable Organolithium Reagents Using Flow Microreactors.

-glycosides are versatile scaffolds for drugs and bioactive compounds. The common organolithium-based synthesis of -glycosides is limited by low reaction temperatures and a restricted substrate scope. To address these issues, a flow microreactor (FMR) was utilized for rapid mixing and precise temperature control, enabling -glycoside synthesis at temperatures up to 40 °C and expanding the substrate scope.

Ligand-Controlled Stereoselective Synthesis and Biological Activity of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands.

Glycoconjugate analogues in which the sp -hybridized C2 position of the carbohydrate structure (normally bearing a hydroxy group) is converted into a compact sp -hybridized exomethylene group are expected to have unique biological activities. We established ligand-controlled Tsuji-Trost-type glycosylation methodology to directly prepare a variety of these 2-exomethylene pseudo-glycoconjugates, including glucosylceramide analogues, in an α- or β-selective manner. Glucocerebrosidase GBA1 cleaves these synthetic pseudo-β-glucosylceramides similarly to native glucosylceramides.

7-Hydroxy-3-methyleneisoindolin-1-one as a New ESIPT-Fluorescent Probe to Monitor Aqueous Environments.

A 7-hydroxy derivative of 3-methyleneisoindolin-1-one 1 was synthesized and its properties as a new fluorophore undergoing excited-state intramolecular proton transfer (ESIPT) were investigated. In alcohols and dimethylsulfoxide, 1 exhibited dual emission at ca. 380 and 525-540 nm when excited at ca.