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Large scale synthesis of the acetonides of l-glucuronolactone and of l-glucose: easy access to l-sugar chirons |
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| Authors: | Alexander C Weymouth-Wilson Daniel Best Maria-Soledad Pino-González |
| Institution: | a Dextra Laboratories Ltd, The Science and Technology Centre, Whiteknights Road, Reading RG6 6BZ, UK b Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK c Summit PLC, 91, Milton Park, Abingdon, Oxon OX14 4RY, UK d Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias, Universidad de Málaga, 29071 Málaga, Spain |
| Abstract: | 1,2-O-Isopropylidene-α-l-glucurono-3,6-lactone may be synthesized on a 100-200 g scale from cheaply available d-glucoheptonolactone in an overall yield of 94% in four steps via l-glucuronolactone. Subsequent elaboration to l-glucose, diacetone-l-glucose (1,2:5,6-di-O-isopropylidene-α-l-glucofuranose), and monoacetone-l-glucose (1,2-O-isopropylidene-α-l-glucofuranose) allows easy access to a range of l-sugar chirons. |
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