Acid-catalysed hydrolysis of 1,2- O-alkylidene-α- d-glucofuranoses

The rates of acid-catalysed hydrolysis of 1,2- O-alkylidene-α- d-glucofuranoses indicate that, for oligosaccharide synthesis, cyclopentylidene and cycloheptylidene acetals are better protecting groups than the isopropylidene residue. Hydrolysis was impeded by a nitrate group at position 5 and more s...

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Bibliographic Details
Published in:Carbohydrate research 1977-01, Vol.58 (2), p.337-344
Main Authors: van Heeswijk, Wolfgang A.R., Goedhart, Johannes B., Vliegenthart, Johannes F.G.
Format: Article
Language:English
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Summary:The rates of acid-catalysed hydrolysis of 1,2- O-alkylidene-α- d-glucofuranoses indicate that, for oligosaccharide synthesis, cyclopentylidene and cycloheptylidene acetals are better protecting groups than the isopropylidene residue. Hydrolysis was impeded by a nitrate group at position 5 and more so by one at position 3. The hydrolyses were accompanied by a positive drift in optical rotation, except for the 5- O-substituted compounds where the formation of d-glucopyranose derivatives cannot occur.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)84360-8