ABSTRACT
Experimental Methods ........................................................................................... 378 General Methods ............................................................................................... 378
O-(2,3,4-Tri-O-Acetyl-6-Deoxy-α-l-Galactopyranosyl)-NHydroxyphthalimide (2) and O-(2,3,4-Tri-O-Acetyl-6-Deoxy-β-lGalactopyranosyl)-N-Hydroxyphthalimide (3) ............................................ 379 O-(6-Deoxy-α-l-Galactopyranosyl)Hydroxylamine (O-α-l-Fucopyranosylhydroxylamine) (4) ...................................................380 O-(6-Deoxy-β-l-Galactopyranosyl)Hydroxylamine (O-β-l-Fucopyranosylhydroxylamine) (5) ...................................................380
Acknowledgments .................................................................................................. 381 References .............................................................................................................. 385
In the last decade, chemoselective oxime ligation has proved to be an attractive synthetic strategy in glycochemistry.1 For example, many glycosylhydroxylamines have been ef¥ciently conjugated through oxime linkage to aldehyde or ketone-containing biomolecules such as peptides2 or oligonucleotides.3 These key building blocks were also shown useful for the preparation of combinatorial libraries4 and antitumoral synthetic vaccines,5 for the immobilization of glycoclusters on surfaces,6 for chemical engineering,7 or for the construction of diverse other neoglycoconjugates.8 Thus, a simple and ef¥cient synthetic method that ensures direct incorporation of anomeric hydroxylamine functionality is essential to achieve that purpose.
