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Paper | Regular issue | Vol 41, No. 4, 1995, pp.697-707
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6957
Synthesis and Characterization of 6-O-α- and 6-O-β-D-Glucopyranosylmorphine and 6-O-β-D-Glucopyranosylcodeine

Pavol Kovác and Kenner C. Rice

*Laboratory of Medicinal Chemistry, NIDDK, Bldg. 8, Rm. B1-23, National Institutes of Health, Bethesda, MD 20892-0815, U.S.A.

Abstract

6-O-α- and β-D-glucopyranosylmorphine and 6-O-β-D-glucopyranosylcodeine have been prepared by condensations of 2,3,4,6-tetra-O-acyl-α-D-glucopyranosyl bromides with 3-O-acetylmorphine and codeine, respectively, followed by deprotection. Depending upon the method of condensation, variable amounts of orthoesters were found among the final products of condensation together with the desired glycosides. Highest yields of glycosides were obtained when 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide was the glycosyl donor, and when the condensation was promoted with silver triflate in the presence of a less than stoichiometric amount of 2,4,6-trimethylpyridine as the acid scavenger.