4,6-O-benzylidene-D-glucopyranose and its sodium salt: new data on their preparation and properties

An improved method for the preparation of 4,6-O-benzylidene-D-glucopyranose (BG), and new or correlated data on its 1H and 13C NMR spectra, specific rotations, and tautomeric equilibria, and on those of its anomeric sodium salt (BGNa), are reported. Evidence is presented in favour of the hypothesis...

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Bibliographic Details
Published in:Carbohydrate research 1995-11, Vol.278 (1), p.43-57
Main Authors: Barili, P L, Berti, G, Catelani, G, Cini, C, D'Andrea, F, Mastrorilli, E
Format: Article
Language:English
Subjects:
Acetylation
Acylation
Antineoplastic Agents - chemical synthesis
Carbohydrate Conformation
Carbohydrate Sequence
Disaccharides - chemical synthesis
Glucose - analogs & derivatives
Glucose - chemical synthesis
Glucose - chemistry
Isomerism
Magnetic Resonance Spectroscopy
Methylation
Molecular Sequence Data
Salts
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Summary:An improved method for the preparation of 4,6-O-benzylidene-D-glucopyranose (BG), and new or correlated data on its 1H and 13C NMR spectra, specific rotations, and tautomeric equilibria, and on those of its anomeric sodium salt (BGNa), are reported. Evidence is presented in favour of the hypothesis that crystalline BGNa exists entirely in its beta-anomeric form and that it can be useful in the access to beta-glucosides in reactions with strong electrophiles under strictly heterogeneous conditions.
ISSN:0008-6215
DOI:10.1016/0008-6215(95)00227-8