Synthesis of 3- and 4-deoxy derivatives of L-rhamnose from 1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

Article abstract of DOI:10.1016/0008-6215(94)80045-6

The 3,6- and 4,6-dideoxyhexoses are biological important carbohydrates frequently found as constituents of specific lipopolysaccharides in the cell walls of gram-negative bacteria, where they commonly appear at the reducing terminus and contribute in many cases to the serological specificity of the bacterial antigen. We were interested in 3- and 4-deoxygenated analogues of L-Rhamnose in connection with a synthesis of deoxygenated analogues of the trisaccharide component of the repeating unit of the capsular polysaccharide of Streptococcus pneumoniae type.