A delta-dicarbonyl heptose has been prepared through an electrophilic ring opening procedure of a 5'spirocyclopropanated lactose derivative. The reported synthetic procedure outlines a new route for the transformation of this renewable disaccharide into new and interesting delta-dicarbonyl sugars, synthetic precursors of cyclitols, carba-and azasugars. The experimental results of the cyclopropanation process have been successfully rationalized by in silico studies. (C) 2016 Elsevier Ltd. All rights reserved.

5 '-Spiro-cyclopropanated lactose derivatives as suitable intermediates for the chain elongation: synthesis of a new 6-deoxy-6-methyl delta-eptulose

PISTARA', Venerando;RESCIFINA, Antonio;
2016-01-01

Abstract

A delta-dicarbonyl heptose has been prepared through an electrophilic ring opening procedure of a 5'spirocyclopropanated lactose derivative. The reported synthetic procedure outlines a new route for the transformation of this renewable disaccharide into new and interesting delta-dicarbonyl sugars, synthetic precursors of cyclitols, carba-and azasugars. The experimental results of the cyclopropanation process have been successfully rationalized by in silico studies. (C) 2016 Elsevier Ltd. All rights reserved.
delta-dicarbonyl heptose; Chain elongation; In silico studies; Lactose; Cyclopropanation
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/17724
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