Acta Pharm. 49 (1999) 11-19

Original scientific paper  
 

Synthesis of 5-hydroxymethylbenzopsoralen glucoside

BRANKA ZORC,*1  MILENA JADRIJEVIC-MLADAR TAKAC, 1 and  PAOLO RODIGHIERO2

1Faculty of Pharmacy and Biochemistry,  University of Zagreb,  Zagreb,  Croatia
2Centre for Chemical Investigation of Drugs of CNR,  Associated with the National Institute for the
Chemistry of Biological Systems – CNR,  Padova,  Italy
Received  December 7, 1998      Accepted  February 8, 1999

Benzopsoralen derivative, 5-hydroxymethyl-2H-benzofuro[3,2-g]-1- benzopyran-2-one (BP-OH, 1) and its 5-bromomethyl analogue (BP-Br, 3) were transformed to the corresponding glucoside, 5-(2,3,4,6-tetra-O-beta-D- glucopyranosyloxymethyl)-2H-benzofuro[3,2-g]-1-benzopyran-2-one (benzopsoralenacetylated glucoside, BP-OAG, 7), which after deacetylation yielded the free glucoside 8. Different synthetic approaches were tried to accomplish glycosidation, including Ag2 CO3, HgO/HgCl2, Hg(CN)2 or BF3×Et2O as aglycone and carbohydrate moiety condensation promotors. Hg(CN)2 was found to give significantly better yield (70%) on the product 7 than other mercury and silver salts or BF3×Et2O.

Keywords: benzopsoralen glucoside, 5-(beta-D-glucopyranosyloxymethyl) -2H-benzofuro[3,2-g]-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction