Preparation of 1,2-O-isopropylidene derivatives of alpha-D-galactoseptanose, beta-L-altroseptanose, and 3-O-methyl-alpha-D-guloseptanose |
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Authors: | Driver G E Stevens J D |
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Institution: | School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia. |
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Abstract: | Displacement of the tosyloxy group in 5-O-benzyl-1,2-O-isopropylidene-4-O-(p-toluenesulfonyl)-alpha-D-glucoseptanose has yielded derivatives of 1,2-O-isopropylidene-alpha-D-galactoseptanose. Acid catalysed acetonation then gave 1,2:3,4-di-O-isopropylidene-alpha-D-galactoseptanose or 1,2;4,5-di-O-isopropylidene-alpha-D-galactoseptanose using lower acid concentrations. Reduction of the ketone derived from 1,2:3,4-O-isopropylidene-alpha-D-septanose gave 1,2;3,4-di-O-isopropylidene-beta-L-altroseptanose. Reaction of 3,4-anhydro-5-O-benzyl-1,2-O-isopropylidene-alpha-D-galactoseptanose with sodium methoxide gave 5-O-benzyl-1,2-O-isopropylidene-4-O-methyl-alpha-D-glucoseptanose and 5-O-benzyl-1,2-O-isopropylidene-3-O-methyl-alpha-D-guloseptanose. Solution-state conformations of these compounds have been deduced from their 1H NMR spectra. |
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