Synthesis of Hydroxylated Analogues of α-Galactosyl Ceramide (KRN7000)with Varying Stereochemistry

The synthesis of analogues of α-galactosyl ceramide (KRN7000) with an additional hydroxy group in the phytosphingosine chains and with varying stereochemistry is described. Careful selection of glucose, galactose, mannose, and talose hexopyranoses allowed us to control the stereochemistry of some of the hydroxy groups in the sphingosine chain to give some interesting hydroxylated KRN7000 analogues