Collect. Czech. Chem. Commun. 1985, 50, 2000-2009

Reaction of 1,6-anhydro-4-O-benzyl-2-deoxy-2-isothiocyanato-β-D-glucopyranose; Preparation of 2-amino-1,6-anhydro-2,3-dideoxy-2,3-dideoxy-β-D-ribo-hexopyranose

Tomáš Elberta and Miloslav Černýb

a Institute for Research, Production and Application of Radioisotopes, 102 27 Prague 10
b Department of Organic Chemistry, Faculty of Natural Sciences, Charles University, 128 40 Prague 2


1,6-Anhydro-4-O-benzyl-2-deoxy-2-isothiocyanato-β-D-glucopyranose (IV), prepared from 2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose (I) by reaction with carbon disulfide followed by oxidation with iodine, was converted into the 3-O-p-toluenesulfonate VII. This was cyclized to give either the 2,3-epimino derivative X or the thiazoline XII. 2-Acetamido-3-S-acetyl-1,6-anhydro-4-O-benzyl-2-deoxy-3-thio-β-D-glucopyranose (XVI), obtained from compound XII, was desulfurized with Raney nickel to afford 2-acetamido-1,6-anhydro-2,3-dideoxy-β-D-ribo-hexopyranose (XVII). The isothiocyanato group was not affected upon acetylation of compound IV and acetolysis of the 1,6-anhydride bond with acetic anhydride and trifluoroacetic acid.