1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-α-L-sorbofuranose
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Turner, P
Kato, A
Houston, TA
Simone, MI
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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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Acta Crystallographica. Section E Structure Reports Online
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E69
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© The Author(s) 2013. For information about this journal please refer to the journal’s website. All articles published in Acta Crystallographica Section E are open access and distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. See http://creativecommons.org/licenses/by/2.0/uk/legalcode
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Chemical sciences
Organic chemical synthesis