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

Journal article

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. © 2009 Elsevier Ltd. All rights reserved.

Authors: Weymouth-Wilson, A; Clarkson, R; Jones, N; Best, D; Wilson, F

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 50
• Issue: 46
• Pages: 6307-6310
• Publication date: 2009-11-18
• DOI: 10.1016/j.tetlet.2009.08.124
• ISSN: 0040-4039
• Language: English