Mixed-acetal glycosides. The preparation and configurational assignment of (R)- and (S)-2-bromo-1-methoxyethyl α-d-glucopyranoside and derivatives thereof

Add time:09/06/2019    Source:sciencedirect.com

By proton-catalyzed transacetalation with 2-bromoacetaldehyde dimethyl acetal as the substrate and 2,3,4,6-tetra-O-acetyl-d-glucose as the acceptor, a mixture of diastereoisomeric, mixed-acetal glycosides was obtained. α-Glycosides preponderated, and could be separated by chromatography into (R)- and (S)-2-bromo-1-methoxyethyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside. Structural assignment was achieved via the intramolecular, nucleophilic-cyclization products (6S)- and (6R)-6-methoxy-(3,4,6-tri-O-acetyl-α-d-glucopyrano)-[1,2-b]-1,3-dioxane. Several derivatives could be prepared by functionalizing the aglycon group.

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