Glycoconjugated Porphyrins. 3. Synthesis of Flat Amphiphilic Mixed meso-(Glycosylated aryl)porphyrins and Mixed meso-(Glycosylated aryl)alkylporphyrins Bearing Some Mono- and Disaccharide Groups

Article abstract of DOI:10.1021/jo00111a013

p-Acetylglycosylated benzaldehydes react with pyrrole by Lindsey's method to produce a variety of flat glycosylated porphyrins.By the same method a large series of amphiphilic mixed glycosylated arylaryl- and mixed glycosylated arylalkylporphyrins have been synthesized, using pyrrole, p-acetylglycosylated benzaldehyde and aryl aldehyde or alkyl aldehyde as starting materials.Under optimized conditions, the di- or teiglycosylated derivatives were principally obtained whereas the formation of meso tetrasubstituted porphyrins is minimized.Deprotection of acetyl glycoside moieties allows us to obtain products with good solubility in neutral aqueous solution and a wide range of amphiphilic character.The structure of these new protected and unprotected compounds in solution was confirmed by 1H NMR studies.