Pseudosugars, 35. Synthesis of glycosylceramide analogs composed of imino‐linked unsaturated 5a‐carbaglycosyl residues: Potent and specific gluco‐ and galactocerebrosidase inhibitors

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Abstract
5a‐Carba‐β‐glucosyl‐ E‐3 and galactosylceramide analogs E‐4 were synthesized by coupling of the protected derivatives 5 of β‐valienamine and 15 of 4‐epi‐β‐valienamine with the aziridines E‐6 and Z‐6, as the sphingosine precursors, respectively, and subsequent deprotection and N‐acylation. Both the new analogs and their corresponding Z‐isomers Z‐3 and Z‐4 were shown to be very potent and specific gluco‐ and galactocerebrosidase inhibitors, and, interestingly, the Z‐isomers possess inhibitory activity comparable to that of the corresponding E‐isomers.

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