A one pot synthesis of mono- and di-lactosyl sphingosines.
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.
Zhang
Y
Y
Division of Biomembrane Research, Pacific Northwest Research Institute, 720 Broadway, Seattle, Washington 98122-4327, USA. yongmin.zhang@ens.fr
Toyokuni
T
T
Ruan
F
F
Hakomori
S I
SI
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D011609:Psychosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment
C023601:lactosylsphingosine; D011609:Psychosine