Ketals of -rhamnoheptonolactones: Potential mimics of -rhamnose |
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Authors: | Joseph R. Wheatley Annabel R. Beacham Paul M. de Q. Lilley David J. Watkin George W. J. Fleet |
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Affiliation: | Joseph R. Wheatley, Annabel R. Beacham, Paul M. de Q. Lilley, David J. Watkin,George W. J. Fleet, * |
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Abstract: | Isopropylidene and cyclohexylidene ketals of γ- and δ-heptonolactones derived from Kiliani ascensions of protected L-rhamnose may constitute suitable intermediates for the preparation of mimics of L-rhamnose. The X-ray crystal structure of 7-deoxy-3,4-O-isopropylidene-L-glycero-L-galacto-heptono-1,5-lactone provides an example of a δ-lactone in a boat conformation with a substituent in a flagpole position. The size of ring in the lactones is completely consistent with Hudson's classical lactone rotation rule of 1910. |
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