Comparison of the two anomers of methyl 2-(N-benzyl­amino)-2,3-di­deoxy-4,6-O-phenyl­methyl­ene-3-C-phenyl­sulfonyl-D-gluco­pyran­oside

Abstract

The title compounds, the α and β anomers of methyl 2-(N-benzyl­amino)-2,3-di­deoxy-4,6-O-phenyl­methyl­ene-3-C-phenyl­sulfonyl-D-gluco­pyran­oside, C₂₇H₂₉NO₆S, belong to the class of deoxy­amino-­sugars prepared by the addition of amines at C2. The endocyclic bond lengths of the pyran­ose ring in the α anomer are shorter than the corresponding bonds in the β anomer. The pyran­ose ring is in the chair form in the former, while it is in the boat form in the latter. These observed differences could be attributed to the C2 substitution of a bulky group. The phenyl­sulfonyl and benzyl­amino groups are in equatorial positions in the α anomer, while the benzyl­amino group is axial in the β anomer.