Synthesis of 1,2,3-tri-O-β-lactosyl-d-threitol and 1-O-benzyl-2,3,4-tri-O-β-lactosyl-d-threitol

The coupling of 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-α-lactosyl bromide with 1,4-di-O-benzyl-d-threitol using mercury(II) cyanide as a promoter, with subsequent deprotection of one or both of the benzyl groups, further glycosylation, and deacetylation afforded the title compounds. This class of compound is useful in the assessment of binding properties of d-galactopyranose to human and rabbit hepatocytes.