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Total synthesis of ceramide trihexoside accumulating with fabry's disease

1978; Elsevier BV; Volume: 22; Issue: 3 Linguagem: Inglês

10.1016/0009-3084(78)90026-9

1873-2941

David J. Shapiro, A. J. Acher,

Sphingolipid Metabolism and Signaling

We report the synthesis of natural ceramide trihexoside, viz. gal (alpha-1 leads to 4) gal (beta-1 leads to 4) gluc (beta-1 leads to 1) ceramide (XIII). It involves the Koenigs-Knorr reaction of the bromide II with the aglucon XIX, and of the chloride VII with the D-enantiomer of the ceramide ester XII. A positional isomer of XIII was obtained as a by-product. A novel technique in the Koenings-Knorr reaction is described.