Abstract
Galactofuranose-disaccharide analogues incorporating a 1,4-dideoxy-1,4-imino- d-galactitol moiety were obtained by 1,3-dipolar cycloadditions of a galacto-configured cyclic nitrone with arabino- or galacto-furanosides carrying a C-vinyl or O-allyl substituent. Remarkably, the cycloadditions could be performed highly efficiently and stereoselectively in water using unprotected nitrone and sugar-derived dipolarophile as reaction partners. The resulting pseudo-disaccharides are analogues of the Gal f-Gal f motifs found in mycobacterial cell-wall glycans and therefore constitute mimics of the acceptor substrates of mycobacterial Gal f-transferases.
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