Research Article: Redetermination of methyl 3,4-O-isopropyl­idene-β-D-fucopyran­oside monohydrate

Date Published: May 01, 2009

Publisher: International Union of Crystallography

Author(s): Hoong-Kun Fun, Samuel Robinson Jebas, Sankappa Rai, Prakash Shetty, Arun M Isloor.


In the title compound, C10H18O5·H2O, the fucopyran­oside ring adopts a chair conformation. The crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯O hydrogen bonds together with intra­molecular O⋯O [2.2936 (8) Å] and inter­molecular O⋯O [2.7140 (8)–2.829 (3) Å] short contacts. The mol­ecules are linked together to form an infinite chain along the a axis. This structure has been solved previously but with no R-values [Spiers (1931). Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem.78, 101].

Partial Text

D-fucose (6-de­oxy-D-galactose) is an effective gratuitous inducer of the galactose operon in Escherichia coli, see: Musso et al. (1963 ▶). 6-Deoxy­hexose and its derivatives are important components of lipopolysaccharides, see: Bilge et al. (1996 ▶); Villeneuve et al. (2000 ▶); Wu & Mackenzie (1987 ▶); Caroff, Bundle & Perry (1984 ▶); Caroff, Bundle, Perry, Cherwonogrodzky & Dunch (1984 ▶). For a previous structure determination of the title compound, see: Spiers (1931 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).




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