Selectivity of 1-O-Propargyl-d-Mannose Preparations

Abstract

Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.

Thermo-switchable hydrophobic deep eutectic solvent for CuAAC

“…High-resolution mass spectra (HRMS) were obtained using time-of-flight (TOF) and orbitrap MS. Copper contamination was determined using an ICP-OES Agilent 5800 equipment. 1-Azido-propane-3-ol, 15 2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl azide, 16 1- O -propargyl- d -mannose, 17 and SIMesCuCl 18 were synthesised from procedures reported in literature.…”

“…1-Azido-propane-3-ol, 15 2,3,4,6-tetra-O-acetyl-b-Dgalactopyranosyl azide, 16 1-O-propargyl-D-mannose, 17 and SIMesCuCl 18 were synthesised from procedures reported in literature.…”