PREPARATION OF O-HYDROXYETHYL AND O-HYDROXYPROPYL DERIVATIVES OF D-GLUCOSE AND 2-ACETAMIDO-2-DEOXY-D-GLUCOSE FOR STUDIES OF MODIFIED HYALURONIC-ACID

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2- acetamido-2-deoxy-D-glucose have been synthesized for use as reference substances for structural studies of hydroxyethylated and hydroxyprop ylated hyaluronic acid. Hydroxyethyl and hydroxypropyl substituents we re introduced in the 2-O- or 3-0-position Of D-glucose and in the 4-0- or 6-0-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suit ably protected sugars with either ethylene oxide or propylene oxide. F or hydroxyethyl derivatives yields varied between 21 and 74% and with a substantial portion of the doubly alkylated compounds. For hydroxypr opyl derivatives yields varied between 15 and 80%. Only trace amounts or the doubly alkylated compounds were found. The proportions of the r espective derivatives were estimated using GLC-MS. All products were c haracterized by H-1 and C-13 NMR spectroscopy.