Synthesis and Characterization of 6-O-a- and 6-O-b-D-Glucopyranosylmorphine and 6-O-b-D-Glucopyranosylcodeine
Year: 1995
Type: article
Abstract: 0 -a -and P-D-glucopyranosylmorphine and 6 -0 -P -Dglucopyranosylcodeine have been prepared by condensations of 2,3,4,6-tetra-0acyl-a-D-glucopyranosyl bromides with 3-0-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-0-benzoyl-WL-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 2,4,6trimethylpyridine as the acid scavenger.
Source: Heterocycles
DOI: 10.3987/com-94-6957
Authors: Pavol Kovác, Kenner C. Rice
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W2952332397