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

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.

Figure 1

View of the title mol­ecule, drawn with 25% probability displacement ellipsoids.

Figure 2

The unit-cell contents viewed along approximately the b axis. Some inter­molecular binding contacts are shown as blue dotted lines. [Symmetry codes: (i) −x, y + , 1 − z; (ii) 1 − x, y − , 1 − z; (iii) 1 − x, y + , 1 − z.]

Figure 3

The O6—N1—C1—O1 and C9—O6—N1—C1 torsion angles of N-glycosyl­oxyamines: left – title compound; middle – N-β-gluco­pyran­osyl­oxy­amine (Langenhan et al., 2005 ▸); right – N-β-galacto­pyran­osyl­oxy­amine (Renaudet & Dumy, 2002 ▸).