title: 1-O-Benzyl-2,3-O-iso-propyl-idene-6-O-tosyl-α-l-sorbo-furan-ose.
abstract: {(3aS,5S,6R,6aS)-3a-[(benz-yloxy)meth-yl]-6-hy-droxy-2,2-di-methyl-tetra-hydro-furo[2,3-d][1,3]dioxol-5-yl}methyl 4-methyl-benzene-sulfonate), 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 furan-ose ring adopts a slightly twisted envelope conformation (with the C atom bearing the methyl-benzene-sulfonate 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, mol-ecules pack in columns along [010] linked by O-H⋯O hydrogen bonds involving the furan-ose hy-droxy group and furan-ose ether O atom.
authors.affiliation: School of Chemistry (F11), University of Sydney, NSW 2006, Australia.
authors.forename: John H
authors.initials: JH
authors.lastname: Reed
authors.forename: Peter
authors.initials: P
authors.lastname: Turner
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Todd A
authors.initials: TA
authors.lastname: Houston
authors.forename: Michela I
authors.initials: MI
authors.lastname: Simone
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