THE SYNTHESIS OF ESTRIOL 16-MONOGLUCURONIDE AND 17-MONOGLUCURONIDE FROM ESTRIOL

An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved b y the selective protection and deprotection of the hydroxy groups in e striol, Koenigs-Knorr reactions with methyl deoxy-2,3,4-tri-O-acetyl-a lpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (H-1 NMR), two -dimensional H-1 homonuclear shift-correlated spectra (2D-COSY) and ma ss spectra. The selective Koenigs-Knorr reaction of the alcoholic hydr oxyl group in the presence of a phenolic hydroxyl group is also report ed.