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.
Highlights
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 dioxalane ring is in a flattened envelope conformation with the fused CH C atom as the flap
Molecules pack in columns in the [010] direction linked by O—H···O hydrogen bonds invovling the furanose hydroxy group and furanose ether oxygen atom (Fig. 3)
Summary
& Martin (2007); Pollock et al (2008). For the synthesis of 1-O-benzoyl-2,3-O-isopropylidene-6-O-tosyl--l-sorbofuranose, which bears structural similarity to the title compound, see: Fehér & Vargha (1966). 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 The dioxalane ring is in a flattened envelope conformation with the fused CH C atom as the flap. Linked by O—H O hydrogen bonds involving the furanose hydroxy group and furanose ether O atom
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