Cerebroside analogues from 3-phenylserines.
Cerebroside analogues were synthesized from DL-threo-and DL-erythro-3-phenylserines by the following sequence of reactions: esterification, N-acylation, reduction with sodium bis (2-methoxyethoxy)-aluminum hydride (SMEAH), and condensation with acetobromoglucose followed by deacetylation. Mass spectrometry disclosed that the glycosidic bond was formed at the primary hydroxyl group.
D002554:Cerebrosides / Q000138:chemical synthesis*; D004952:Esters; D013058:Mass Spectrometry; D008722:Methods; D012694:Serine / Q000031:analogs & derivatives*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D002554:Cerebrosides; D004952:Esters; D012694:Serine