PubMed:11403083 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PubMed/sourceid/11403083","sourcedb":"PubMed","sourceid":"11403083","source_url":"http://www.ncbi.nlm.nih.gov/pubmed/11403083","text":"Synthesis of C-mannopyranosylphloroacetophenone derivatives and their anomerization.\nThe reaction of 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranosyl fluoride (6-deoxy-2,3,4-tri-O-benzyl-alpha-L-mannopyranosyl fluoride) with 2,4-dibenzylphloroacetophenone, in the presence of boron trifluoride.diethyl etherate, afforded both the 3-C-alpha-L- and the 3-C-beta-L-rhamnopyranosylphloroacetophenone derivatives. The 3-C-alpha-L-rhamnoside was produced as a major product, while the 3-C-beta-L-rhamnoside was produced as a minor product via anomerization of the 3-C-alpha-L-rhamnoside. Alternatively, the reaction of 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranosyl fluoride with 2,4-dibenzylphloroacetophenone afforded both the 3-C-alpha-D- and the 3-C-beta-D-mannnopyranosylphloroacetophenone derivatives under identical conditions. The 3-C-beta-D-mannoside was produced as a major product via anomerization of the 3-C-alpha-D-mannoside during the reaction. These differences in composition result apparently from the magnitude of the 1,3-diaxial interactions between the C-3 and C-5 positions in these sugar 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