Synthese von Undecose‐Derivaten als D ‐Galactose‐Analoga zur spezifischen Modifikation Galactose‐bindender Proteine

Syntheses of Undecose Derivatives as D ‐Galactose Analogues for Specific Modification of Galactose‐Binding Proteins A series of undec‐ and dodecoses containing functional groups was obtained from 1,2:3,4‐di‐ O ‐isopropylidene‐α‐ D ‐ galacto ‐hexodialdo‐pyranose‐(1,5) ( 1 ) using Wittig and Grignard reactions to bring about chain elongation. The compounds resemble 6‐ C ‐alkylated D ‐galactose derivatives which should have affinity to some galactose‐binding proteins. One potential photoaffinity reagent, 8‐azi‐6,7,8,9,10‐pentadeoxy‐ D ‐ galacto ‐undecose ( 12 ), was prepared from 6,7,9,10‐tetradeoxy‐1,2:3,4‐isopropylidene‐α‐ D ‐ galacto ‐8‐undecosulopyranose‐(1,5) ( 10 ). Compound 11 is suitable for syntheses of “spacer‐modified” oligosaccharides.