(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide

Acta Crystallographica Section E

Structure Reports Online

Volume 66, Part 11 (November 2010)

organic compounds

hb5639 scheme

Acta Cryst. (2010). E66, o2750-o2751 [ doi:10.1107/S1600536810039589 ]

(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide

M. I. Simone, A. A. Edwards, A. R. Cowley, G. W. J. Fleet and D. J. Watkin

Abstract: X-ray crystallographic analysis with Cu K [alpha] radiation established the relative configurations of the stereogenic centers in the title compound, C₁₅H₂₀N₂O₅, and clarified mechanistic ambiguities in the synthesis. The conformation of the five-membered ring approximates twisted, about a C-O bond. The absolute configuration of this carbon-branched dipeptide isostere was known based on the use of D-ribose as the starting material. Refinement of the Flack parameter gave an ambiguous result but the refined Hooft parameter is in agreement with the assumed (D-ribose) absolute structure. The crystal structure consists of N-HO and O-HO hydrogen-bonded bi-layers, with the terminal methyl and phenyl groups forming a hydrophobic inter-layer interface. Some weak C-HO interactions are also present.