5′-Spiro-cyclopropanated lactose derivatives as suitable intermediates for the chain elongation: synthesis of a new 6-deoxy-6-methyl δ-eptulose. (3rd March 2016)

• Record Type: Journal Article
• Authors: Pistarà, Venerando; Rescifina, Antonio; Corsaro, Antonino
• Is Part Of: Carbohydrate research. Volume 422(2016)
• Page Start: 45
• Page End: 52
• Publication Date: 2016-03-03
• Subjects: δ-dicarbonyl heptose -- Chain elongation -- Lactose -- Cyclopropanation -- In silico studies; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2016.01.008
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: New route for the synthesis of δ-dicarbonyl heptose. Hex-5′-enopyranoside cyclopropanation by ethoxycarbonyl carbene addition. The experimental results have been rationalized with computational calculations. Semiempirical PM6-D3 Hamiltonian achieve results where DFT calculations fails. Graphical abstract: Abstract: A δ-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 δ-dicarbonyl sugars, synthetic precursors of cyclitols, carba- and azasugars. The experimental results of the cyclopropanation process have been successfully rationalized by in silico studies.