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

Venerando Pistarà; Antonio Rescifina; Antonino Corsaro

doi:10.1016/j.carres.2016.01.008

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

Carbohydr Res. 2016 Mar 3:422:45-52. doi: 10.1016/j.carres.2016.01.008. Epub 2016 Jan 25.

Authors

Venerando Pistarà¹, Antonio Rescifina², Antonino Corsaro²

Affiliations

¹ Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, I-95125 Catania, Italy. Electronic address: [email protected].
² Dipartimento di Scienze del Farmaco, Università di Catania, viale A. Doria 6, I-95125 Catania, Italy.

PMID: 26854721
DOI: 10.1016/j.carres.2016.01.008

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.

Keywords: Chain elongation; Cyclopropanation; In silico studies; Lactose; δ-dicarbonyl heptose.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Chemistry Techniques, Synthetic
Lactose / analogs & derivatives*
Lactose / chemical synthesis
Lactose / chemistry*
Models, Molecular
Spiro Compounds / chemistry*

Substances

6-deoxy-6-methyl delta-eptulose
Spiro Compounds
Lactose