P. Murphy, C. McDonnell, Ludger Hämig
Jan 6, 2003
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Influential Citations
16
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra- O -( tert -butyldimethylsilyl)- d -glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo -glycal derivatives of these lactones using the Ramberg–Backlund rearrangement of the corresponding sulfones.