Regioselective Synthesis of Novel Mono-Substituted D-lactose Fatty Acid Ester Derivatives

High-energy collision-induced dissociation tandem mass spectrometry of regioisomeric lactose palmitic acid monoesters using matrix-assisted laser desorption/ionization

“…The lactose monopalimtates studied, 3‐ O ‐palmitoyl‐D‐lactose ( 1 ), 3'‐ O ‐palmitoyl‐D‐lactose ( 2 ) and 6'‐ O ‐palmitoyl‐D‐lactose ( 3 ), illustrated in Fig. , were prepared by the chemical regioselective synthesis of the corresponding lactose derivatives as recently reported . All chemicals were used without further purification.…”

“…have recently reported the chemical regioselective synthesis of lactose monopalmitate regioisomers at different O‐3', O‐6' and O‐3 positions (Fig. ) employing smart protecting group strategy and the chemoselective reactivity of cyclic tin alkoxides . The structural characterization of these well‐defined regioisomers was accomplished using 1 H NMR spectra, 1 H– 1 H COSY experiments, 13 C‐NMR spectra, 13 C– 1 H correlation, and attached proton test (APT) experiments …”