Synthesis of oligosaccharide and peptide using heavy fluorous tag

FLUO 6

Mamoru Mizuno, mmizuno@noguchi.or.jp, Laboratory of Glyco-organic Chemistry, The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo, 173-0003, Japan
A fluorous (highly fluorinated) solvent is immiscible in an organic solution, and a fluorous compound partitions out of an organic phase and into a fluorous phase. Therefore a fluorous compound is readily separated from nonfluorinated compounds by a simple “fluorous/organic” extraction. Curran and his co-workers elaborated the fluorous synthesis (fluorous-tag method) as a strategic alternative to solid-phase synthesis. The strategy of “fluorous synthesis” is designed to combine the advantages of solid-phase synthesis with those of traditional organic synthesis in the liquid-phase synthesis. Our group prepared some kinds of heavy fluorous tags, and reported that syntheses of oligosaccharides, peptides and glycopeptides were achieved efficiently. Recently, a new alkoxyphenyl fluorous tag was used in monosaccharides synthesis and oligosaccharide synthesis. In the synthesis of monosaccharide units, glycosyl acceptor and donor, the triple-chain flurous tag enable easy purification of intermediates and final product using fluorous/organic extraction.