Synthesis of α-S-galactosylceramides with a truncated sphingoid chain

We present here a convenient synthesis of the truncated sphingoid iodide 15 from d-galactose, in which Mitsunobu reaction was utilized to retrieve successfully an unwanted intermediate, thereby increasing greatly the synthetic efficiency. Subsequent reaction of 15 with the pre-prepared α-galactosyl thiol 16 led smoothly to the desired thioglycoside 17 in good yield, from which the catabolically stable thioglycoside analogs of OCH 4 and 22 were synthesized.

Two thioglycoside analogs of α-galactosylceramide with a truncated sphingoid chain were synthesized as potential immunomodulating agents.