N-(2-Acetamido-2-de-oxy-β-d-gluco-pyranos-yl)-N-(3-azido-prop-yl)-O-methyl-hydroxyl-amine

Stefan Munneke; Bridget L Stocker; Mattie S M Timmer; Graeme J Gainsford

doi:10.1107/S2056989016002164

N-(2-Acetamido-2-de-oxy-β-d-gluco-pyranos-yl)-N-(3-azido-prop-yl)-O-methyl-hydroxyl-amine

Acta Crystallogr E Crystallogr Commun. 2016 Feb 17;72(Pt 3):340-2. doi: 10.1107/S2056989016002164. eCollection 2016 Mar 1.

Authors

Stefan Munneke¹, Bridget L Stocker¹, Mattie S M Timmer¹, Graeme J Gainsford²

Affiliations

¹ School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand.
² Callaghan Innovation, PO Box 31-310, Lower Hutt 5040, New Zealand.

Abstract

The structure of the title compound, C12H23N5O6, solved using adequate data from a thin crystal plate, confirmed that this useful glycoconjugate was obtained in the ring-closed β-pyran-ose configuration with (4) C 1 conformation. The mol-ecules are bound by O-H⋯O(OH) hydrogen bonds, notably in a zigzag C(2) chain along the short b (screw) axis, supplemented with an R 2 (2)(12) O-H⋯O(carbon-yl) link along the a axis and other C(2) links. The absolute configuration was not unambiguously determined but was known from the synthetic chemistry, which used natural 2-acetamido-2-de-oxy-d-glucose as the starting material.

Keywords: carbohydrate; crystal structure; oxyamine glycoside.