Large scale synthesis of the acetonides of L-glucuronolactone and of L-glucose: easy access to L-sugar chirons

1,2-O-Isopropylidene-alpha-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-alpha-L-glucofuranose), and monoacetone-L-glucose (1,2-O-isopropylidene-alpha-L-glucofuranose) allows easy access to a range of L-sugar chirons. (C) 2009 Elsevier Ltd. All rights reserved.