Comparison of the two anomers of methyl 2‐(N‐benzylamino)‐2,3‐dideoxy‐4,6‐O‐phenylmethylene‐3‐C‐phenylsulfonyl‐d‐glucopyranoside |
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Authors: | Cheravakkattu G. Suresh Bindu Ravindran K. Narasimha Rao Tanmaya Pathak |
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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. |
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