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 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.
Barili
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PL
Dipartimento di Chimica Bioorganica, Università di Pisa, Italy.
Berti
G
G
Catelani
G
G
Cini
C
C
D'Andrea
F
F
Mastrorilli
E
E
D000107:Acetylation; D000215:Acylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D012492:Salts
D000970:Antineoplastic Agents; D004187:Disaccharides; D012492:Salts; C013844:benzylidene glucose; D005947:Glucose