First Example of a Crystalline Urazole Nucleoside with an L-Configured Sugar. (1S,2S)-Urazole [alpha]-L-Pyranosyl-2-deoxyriboside

The reaction of L-2-deoxyribose with urazole led to the formation of a single crystalline [alpha]-pyranoside diastereomer, (1S,2S)- urazole [alpha]-L-pyranosyl-2-deoxyriboside [IUPAC name: 1-(2-deoxy-[alpha]-L-erythro-pentopyranosyl) 1-(S),2-(S),4-triazolidine-3,5-dione, C₇H₁₁N₃O₅], which is the enantiomer of 1R,2R)-urazole [alpha]-D-pyranosyl-2-deoxyriboside obtained in the analogous reaction with D-2-deoxyribose previously reported. The absolute configurations were ascertained from the known configurations of the 2-deoxyribose moieties. This is the first example of a crystalline urazole nucleoside with an L-configured sugar.

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