1,3,4-Tri-O-acetyl-2-N-(tri-fluoro-acetyl)-β-l-fucose.

Abstract

The title compound, C14H18F3NO8, was produced through conjugation of 1,3,4-tri-O-acetyl-2-azidode­oxy-α,β-l-fucose with tri­fluoro­acetyl chloride in the presence of bis­(di­phenyl­phosphino)ethane in tetra­hydro­furan at room temperature. The X-ray crystal structure reveals that the β-anomer of the product mixture crystallizes from ethyl acetate/hexa­nes. The compound exists in a typical chair conformation with the maximum possible number of substituents, four out of five, located in the sterically preferred equatorial positions. The major directional force facilitating packing of the mol­ecules are N—H⋯O hydrogen bonds involving the amide moieties of neighboring mol­ecules, which connect mol­ecules stacked along the a-axis direction into infinite strands with a C 1 1(4) graph-set motif. Formation of the strands is assisted by a number of weaker C—H⋯O inter­actions involving the methine and methyl H atoms. These strands are connected through further C—H⋯O and C—H⋯F inter­actions into a three dimensional network