De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis

Alex C Comely; Rienk Eelkema; Adriaan J Minnaard; Ben L Feringa

doi:10.1021/ja0347538

De novo asymmetric bio- and chemocatalytic synthesis of saccharides - stereoselective formal O-glycoside bond formation using palladium catalysis

J Am Chem Soc. 2003 Jul 23;125(29):8714-5. doi: 10.1021/ja0347538.

Authors

Alex C Comely¹, Rienk Eelkema, Adriaan J Minnaard, Ben L Feringa

Affiliation

¹ Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

PMID: 12862452
DOI: 10.1021/ja0347538

Abstract

A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides.

Publication types

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

MeSH terms

Acetals / chemistry
Carbohydrates / chemical synthesis*
Carbohydrates / chemistry
Catalysis
Glycosides / chemical synthesis*
Glycosides / chemistry
Palladium / chemistry*
Pyrans / chemistry
Stereoisomerism

Substances

Acetals
Carbohydrates
Glycosides
Pyrans
Palladium