Ethyl 3,6-di-O-benzyl-2-de-oxy-N-phthalimido-1-thio-β-d-glucopyran-oside. 2010

Christoffer Hamark, and Jens Landström, and Lars Eriksson, and Göran Widmalm

In the title compound, C(30)H(31)NO(6)S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thio-ethyl group has the exo-anomeric conformation. The hy-droxy group forms an inter-molecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close π-π contacts with centroid-centroid distances less than 4.0 Å, all with dihedral angles between the inter-acting π systems of only ≃ 8°, supporting energetically favourable stacking inter-actions.

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