Issue 0, 1972

Formation of 3,6-anhydro-4,5-O-isopropylidene-D-allose dimethyl acetal in the methanolysis of 1,2: 5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-α-D-glucofuranose. Synthesis of 3,6-anhydro-D-allose

Abstract

The acid-catalysed methanolysis of 1,2:5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-α-D-glucofuranose yields principally methyl 3-O-p-tolylsulphonyl-α- and -β-D-glucopyranosides, together with a minor amount of 3,6-anhydro-4,5-O-isopropylidene-D-allose dimethyl acetal (VI). Under the same conditions, 1,2-O-isopropyl-idene-5-O-methyl-3-O-p-tolylsulphonyl-α-D-glucofuranose yields 3,6-anhydro-5-O-methyl-D-allose dimethyl acetal in good yield.

3,6-Anhydro-D-allose (IV) and 3,6-anhydro-5-O-methyl-D-allose (V) have been prepared by hydrolysis of the above derivatives and have been found to exist in aqueous solution in aldehydo, aldehydrol (i.e. hydrated aldehyde), and dimeric forms.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 346-351

Formation of 3,6-anhydro-4,5-O-isopropylidene-D-allose dimethyl acetal in the methanolysis of 1,2: 5,6-di-O-isopropylidene-3-O-p-tolylsulphonyl-α-D-glucofuranose. Synthesis of 3,6-anhydro-D-allose

M. H. Randall and S. J. Angyal, J. Chem. Soc., Perkin Trans. 1, 1972, 346 DOI: 10.1039/P19720000346

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