Abstract
The novel 6-deoxy-6- C-sulfo- d-galactose (6-sulfofucose) potassium salt was prepared by oxidation of 1,2,3-tri- O-acetyl-6- S-acetyl-4- O-benzoyl -6-deoxy-α- d-galactopyranose with hydrogen peroxide and potassium acetate in acetic acid. Its cyclohexylammonium salt underwent a spontaneous conversion into 1-cyclohexylamino-1,6-dideoxy- d-tagatofuranose-6- C-sulfonic acid 4 through an Amadori rearrangement. 6-Deoxy-6- C-sulfo- d-glucose (sulfoquinovose) and 6-deoxy-6- C-sulfo- d-galactose were transformed into the corresponding 6-deoxy-6- C-sulfoalditols and 1-amino-1,6-dideoxy-6- C-sulfoalditols by reduction and reductive amination, respectively. The α anomeric configuration of 4, crystallised as the monohydrate, was assigned by X-ray crystallographic analysis. A conformation between E 5 and 4 T 5 for the sugar ring, stabilised by a strong intramolecular hydrogen bond between NH and O-4, was observed.
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