Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 7 (July 2013)


organic compounds



lh5615 scheme

Acta Cryst. (2013). E69, o1069-o1070    [ doi:10.1107/S1600536813015638 ]

1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-[alpha]-L-sorbofuranose

J. H. Reed, P. Turner, A. Kato, T. A. Houston and M. I. Simone

Abstract: In the title compound (systematic name: {(3aS,5S,6R,6aS)-3a-[(benzyloxy)methyl]-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl}methyl 4-methylbenzenesulfonate), C23H28O8S, the absolute structure and relative stereochemistry of the four chiral centres have been established by X-ray crystallography, with the absolute configuration inferred from the use of L-sorbose as the starting material. The central furanose ring adopts a slightly twisted envelope conformation (with the C atom bearing the methylbenzenesulfonate substituent as the flap) from which three substituents depart pseudo-axially (-CH2-O-benzyl, -OH and one acetonide O atom) and two substituents pseudo-equatorially (-CH2-O-tosyl and second acetonide O atom). The dioxalane ring is in a flattened envelope conformation with the fused CH C atom as the flap. In the crystal, molecules pack in columns along [010] linked by O-H...O hydrogen bonds involving the furanose hydroxy group and furanose ether O atom.


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