Research Article: 4-Butyl-1-(2,3,4-tri-O-acetyl-β-l-fuco­pyranos­yl)-1H-1,2,3-triazole

Date Published: August 01, 2009

Publisher: International Union of Crystallography

Author(s): Abdul-Basit Alhassan, Peter Norris, Matthias Zeller.


The title compound, C18H27N3O7, was synthesized by CuI-catalysed coupling of an azide with an alkyne as part of a study into the synthesis of N-glycosyl-1,2,3-triazoles. The crystal structure confirms the selective formation of the β-conformer of the pyran­ose N-glycoside, thus confirming the retention of stereochemistry during heterocycle formation with the N-glycosyl triazole group occupying the equatorial position at the anomeric C atom. The structure exhibits two crystallographically independent mol­ecules (A and B) with essentially identical conformations with a weighted r.m.s. deviation of only 0.09 Å. The mol­ecules are arranged in layers with hydro­phobic and more polar sections built from the butyl triazole units on the one hand and the more polar moieties dominated by the carbohydrate units on the other. Within the polar layers, inter­molecular inter­actions are dominated by a three-dimensional network of weak C—H⋯O hydrogen bonds with the acetyl keto O atoms as the hydrogen-bond acceptors. The triazole units inter­act with each other via C—H⋯N hydrogen bonds which connect the mol­ecules into two infinite chains of mol­ecules made up of either A mol­ecules or B mol­ecules that stretch parallel to each other along [100]. Between the butyl groups no directional inter­actions are observed.

Partial Text

For background information on N-glycosidic mimics of naturally occurring carbohydrates, see: Norris (2008 ▶); Temelkoff et al. (2006 ▶). For details of the synthesis of the carbohydrate starting material used, see: Zhang et al. (2007 ▶).




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