Synthesis of hydroxylated analogues of α-galactosyl ceramide (KRN7000) with varying stereochemistry

Abstract

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. A short, efficient method for the synthesis of hydroxylated analogues of α-galactosyl ceramide (KRN7000) with an extra hydroxy group at the 5-position and altered stereochemistry at the 3-position of the sphingosine moiety is presented. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.