The synthesis of estriol 16- 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 by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported.
Wu
Y
Y
Department of Chemistry & Biochemistry, Massey University, Palmerston North, New Zealand.
Blackwell
L F
LF
D004964:Estriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
C032095:estriol glucuronide; D004964:Estriol