Synthesis of Carbohydrate Derivatives Corresponding to a Tumor-Associated Glycolipid: A Trimeric Lewis X Nonasaccharide and a TrimericN-Acetyl Lactosamine Hexasaccharide

A trimeric Lewis X derivative, p-trifluoracetamidophenylethyl O-(β-D-galactopyranosyl)-(1→4)-O-[3-O-(α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-(1→3)-O-(β-D-galactopyranosyl)-(1→4)-O-[3-O-(α-L-fucopyranosyl)-2-acetamido-2-deoxy-β-D-glucopyranosyl]-(1→3)-O-(β-D-galactopyranosyl)-(1→4)-3-O-(α-L-fucopyranosyl)- 2-acetamido-2-deoxy-β-D-glucopyranoside corresponding to the tumor-associated glycolipid in Figure 1 (n=2), and a trimeric derivative of N-acetyl lactosamine, p-trifluoracetamidophenylethyl O-(β-D-galactopyranosyl)-(1→4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-O-(β-D-galactopyranosyl)-(1→4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-O-(β-D-galacto-pyranosyl)-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside, were synthesised from thioglycoside building blocks. The synthesis was based on intermediates earlier reported.