Coupling of 2,3,6,2′,3′,4′,6′-hepta- O-benzyl-α-lactosyl bromide with an equimolar amount of 1- O-acetyl-2- O-benzyl-( R,S)-glycerols in the presence of tetraethylammonium bromide and 4A molecular sieves in 1,2-dichloroethane afforded 3- O-acetyl-2- O-benzyl-1- O-(2,3,6,2′,3′,4′,6′-hepta- O-benzyl-α-lactosyl)-( R,S)-glycerols in 20.4% yield, which were deprotected to give 1- O-α-lactosyl-( R,S)-glycerols. 2- O-Benzyl-3- O-(2,3,6,2′,3′,4′,6′-hepta- O-acetyl-β-lactosyl)-1- O-(2,3,6,2′,3′,4′,6′-hepta- O-benzyl-α-lactosyl) -( R,S)-glycerols were obtained in 61% yield by the reaction of hepta- O-acetyl-α-lactosyl bromide and 2- O-benzyl-1- O-(2,3,6,2′,3′,4′,6′-hepta- O-benzyl-α- lactosyl)-( R,S)-glycerols in the presence of mercury(II) cyanide in benzene-nitromethane; deprotection afforded 1- O-α-lactosyl-3- O-β-lactosyl-( R,S)-glycerols in an overall yield of 24%. The two target materials are useful in the assessment of the binding properties of d-galactosyl-terminated glyceryl glycosides to the asialoglycoprotein receptor of normal rabbit and human hepatocytes.