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The reaction of 1,2:5,6-di-O-isopropylidene-3-C-methylene-alpha-D-ribo-hexofuranose (4) with mercuric azide in hot 50% aqueous tetrahydrofuran yielded, after reductive demercuration, 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-alpha-D-glucofuranose (5). Partial, acid hydrolysis of 5 afforded the diol 7, which gave 3-azido-3-deoxy-1,2-O-isopropylidene-5,6-di-O-methanesulphonyl-3-C-methyl-alpha-D-glucofuranose (8) on sulphonylation. On hydrogenation over a platinum catalyst and N-acetylation, the dimethanesulphonate 8 furnished 3,6-acetyleprimino-3,6-dideoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-3-C-methyl-alpha-D-glucofuranose (9), which was also prepared by an analogous sequence of reactions on 3-azido-3-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-3-C-methyl-6-O-toluene-p-sulphonyl-alpha-D-glucofuranose (13).
View Article and Find Full Text PDFNEW METHANESULPHONYL SUGAR ALCOHOLS AND THEIR CYTOSTATIC ACTIVITY.
Acta Unio Int Contra Cancrum
December 1996
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