Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

Veerapen et al.

Page 3

Several elegant syntheses of α-GalCer are present in the literature. Most of these syntheses
make use of benzyl ether protecting groups on the sugar moiety. We, along with many other
research groups, have encountered difficulties in the hydrogenolysis of benzyl ethers, thereby
leading to low yields of α-GalCer. Therefore, synthetic routes circumventing the problematic
hydrogenolysis step are highly desired. Kiso and co-workers recently reported such a synthesis,
where interestingly they also made use of the bulky 4,6-O-di-tert-butylsilylene (DTBS) group
as α-directing in galactosylation donor 3.

Published as: BioorgMed Chem Lett. 2009 August 01; 19(15): 4288-4291.

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