Synthesis of phenyl 6'-O-malonyl-beta-D-glucopyranoside. Facile preparation of malonylated glycoconjugates

Regioselective acylation of glycoconjugates with malonic acid was achieved by suing phenyl beta-D-glucopyranoside as a model glycoside, malonic acid, and tert-butyl isocyanide in aprotic solvents. Structural elucidation of phenyl 6'-O-malonyl-beta-D-glucopyranoside was performed by H-1 and C-13 NMR spectroscopy and high-performance liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry; (HPLC-APCI-MS/MS). This one-step reaction opens the way to the preparation of reference substances which are required for the spectroscopic identification of malonylated glycosides in complex natural matrices.