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Cerebroside analogues from 3-phenylserines
Authors:Benjamin Weiss
Affiliation:1. Division of Neuroscience, New York State Psychiatric Institute, Department of Biochemistry, College of Physicians and Surgeons, Columbia University, New York, N.Y. 10032, USA;2. Institute for Neurochemistry and Drug Addiction, Rockland Research Institute, Ward''s Island, N.Y. 10035, USA
Abstract:Cerebroside analogues were synthesized from DL-threo-and DL-erythro-3-phenylserines by the following sequence of reactions: estirification, 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.
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