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The reaction of t -butylmagnesium chlorides with diastereomerically pure ( R )-1,2- O -isopropylidene-3,5- O -sulfinyl-α-d-glucofuranose ( R )- 4 was found to be stopped at the stage of the corresponding, diastereoisomerically pure 1,2- O -isopropylidene-(5- O -α-d-glucofuranosyl) t -butanesulfinate ( S )- 10 for which the crystal structure and the ( S )-absolute configuration was determined by X-ray crystallography. Comparison of the absolute configurations of the starting sulfite ( R )- 4 , and t -butanesulfinate ( S )- 10 (which crystallizes in the orthorhombic system, space group P2 1 2 1 2 1 , with the single compound molecule present in the asymmetric unit), clearly indicates that the reaction of nucleophilic substitution at the stereogenic sulfur atom in the sulfite ( R )- 4 occurs with the full inversion of configuration via the trigonal bipyramidal sulfurane intermediate 4c in which both the entering and leaving groups are located in apical positions.

molecules/molecules online/molecules annual

Diastereoisomerically Pure, (S)-O-1,2-O-isopropyli dene-(5-O-α-d-glucofuranosyl) t-butanesulfinate: Synthesis, Crystal Structure, Absolute Configuration and Reactivity