Methyl 6-azido-6-deoxy-α-D-galactoside

Janice M H Cheng,Graeme J Gainsford,Shivali A Gulab,Bridget L Stocker,Mattie S M Timmer

doi:10.1107/s1600536811025323

Abstract

The structure of the title compound, C7H13N3O5, was solved using data from a multiple fragment crystal. The galactoside ring adopts a 4 C 1 chair conformation. In the crystal, the molecules are linked by strong O—H⋯O hydrogen bonds, which build linkages around the screw axis of the cell in a similar way to the iodo analogue. These C-5 and C-6 packing motifs expand to R 2 2(10), C 2 2(7) and C 2 2 2(8) motifs, as found in closely related compounds.

Highlights

Box 7060, Wellington, New Zealand, and cCarbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
The molecules are linked by strong O—H O hydrogen bonds, which build linkages around the screw axis of the cell in a similar way to the iodo analogue
288 (9)° respectively (Cremer & Pople, 1975) identical to that of the iodo-analogues (Gulab et al, 2010) and similar to that of the corresponding glucopyranoside 0.563 (5) Å, 4.8 (5)° & 310 (5)° (BOSLEB, Sikorski et al, 2009), The absolute configurations known from the synthesis of C1(R), C2(R), C3(S), C4(R) and C5(S) are consistent with the weak indications given by the Hooft parameter (0.0 (2), Hooft et al, (2008)), compared with the indeterminate Flack value of Lattice binding is provided by O—H···O hydrogen bonds (Table 1), which build linkages around the b screw axis of the cell (Figure 2)

Summary

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M. Box 7060, Wellington, New Zealand, and cCarbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand. R factor = 0.047; wR factor = 0.125; data-to-parameter ratio = 7.8. The structure of the title compound, C7H13N3O5, was solved using data from a multiple fragment crystal. The molecules are linked by strong O—H O hydrogen bonds, which build linkages around the screw axis of the cell in a similar way to the iodo analogue. These C-5 and C-6 packing motifs expand to R22(10), C22(7) and C222(8) motifs, as found in closely related compounds. Symmetry codes: (i) x þ 1; y þ 12; z þ 1; (ii) x þ 2; y 12; z þ 1

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