Syntheses of galactose derivatives that are useful in probing the binding specificity of galactosespecific lectins are reported. These include ally1 3-deoxy-and 4-deoxy-j3-D-nylo-hexopyranoside and several disaccharide glycosides having Gal(1 + 2) and Gal(1 + 3) linkages. The p-linked Gal disaccharide isomers were produced using 2,3,4,6-tetra-@acetyl+D-galactopyranosyl bromide as glycosyl donor and the 4,6-0-benzylidene derivatives of ally1 j%D-galactopyranoside, a-o-glucopyranoside, a-o-mannopyranoside, and 2-acetamido-2-deoxy+o-galactopyranoside as acceptors. Only the Gal(1 + 3)-linked disaccharide was obtained when the benzylidene derivatives of the mannopyranoside and 2-acetamido-2-deoxygalactopyranoside were used. Attempts at the preparation of Gal&, l--f 2)Gal and Gal&, 1 + 3)Gal disaccharide glycosides were made using the same strategy, but employing the l-trichloroacetimidate or 1-N-methylacetimidate of 2,3,4,6-tetra-O-benzyl-o-galactopyranose as the glycosyl donor. The latter imidate produced a mixture of Gal(a, 1 + 2)Gal and Gal&, 1 + 3)Gal derivatives as major products, but the former gave the Gal@, 1 + 2)Gal isomer as the major product.