合成路线1

Treatment of 2-(tetradecyl)hexadecyl beta-D-galactopyranoside (I) with benzaldehyde dimethyl acetal (II) in THF containing H2SO4 provides 4,6-O-benzylidene derivative (III), which is then subjected to 3-O-4-methoxybenzylation by reaction with 4-methoxybenzyl chloride (IV), dibutyltin oxide (Bu2SnO) and tetrabutyl ammonium iodide (Bu4NI) in THF to furnish compound (V). On the other hand, phenyl 1-thio-beta-L-fucopyranoside (VI) is regioselectively protected with chloride (IV) by means of dibutyl oxide and tetrabutyl ammonium iodide in THF/MeOH to yield derivative (VII), which is benzylated by means of benzyl bromide (BnBr) and NaH in DMF to give fucopyranoside derivative (VIII). Glycosylation of compound (V) with derivative (VIII) is then performed in the presence of N-iodosuccinimide (NIS), trifluoromethanesulfonic acid (TfOH) and molecular sieves in toluene to afford disaccharide (IX), whose 4-methoxybenzyl groups are removed in CH2Cl2/H2O in the presence of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to yield (X). Sulfation of compound (X) with SO3.pyridine complex in DMF provides sulfate (XI), which is finally hydrogenated over Pd/C in MeOH/THF to furnish the desired product.