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Published on: April 11, 2017
A one pot synthesis of mono- and di-lactosyl sphingosines
1Division of Biomembrane Research, Pacific Northwest Research Institute, 720 Broadway, Seattle, Washington 98122-4327, USA. yongmin.zhang@ens.fr
Abstract:
The importance of analogues of lactosyl ceramides as basic structures of many natural glycosphingolipids provided a rationale for developing an efficient synthetic route to these compounds. We report herein a novel approach to synthesize several members of this family. Glycosylation of N-diphenylmethylene-spingosine, which exists in an imine-oxazolidine tautomeric mixture, with acetobromolactose under a modified Koenigs-Knorr condition yielded lactosyl beta-(1 --> 1) sphingosine, lactosyl beta-(1 --> 3) sphingosine and dilactosyl sphingosine in good yields. A similar glycosylation could be applicable to the synthesis of other glycosphingolipids.
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