Chemoselective Iterative Dehydrative Glycosylation

Hien M Nguyen; Jennifer L Poole; David Y Gin

doi:10.1002/1521-3773(20010119)40:2<414::AID-ANIE414>3.0.CO;2-6

Chemoselective Iterative Dehydrative Glycosylation

Angew Chem Int Ed Engl. 2001 Jan 19;40(2):414-417. doi: 10.1002/1521-3773(20010119)40:2<414::AID-ANIE414>3.0.CO;2-6.

Authors

Hien M Nguyen¹, Jennifer L Poole¹, David Y Gin¹

Affiliation

¹ Department of Chemistry University of Illinois Urbana, IL 61801 (USA) Fax: (+1) 217-244-8024.

PMID: 29712399
DOI: 10.1002/1521-3773(20010119)40:2<414::AID-ANIE414>3.0.CO;2-6

Abstract

The inherent difference in nucleophilicity between alkyl alcohols and free hemiacetals is capitalized upon in a new approach to chemoselective glycosylation. The strategy employs a controlled dehydrative coupling reaction for the rapid assembly of complex oligosaccharides and obviates the need for the extensive protective group and anomeric leaving group differentiation that is traditionally required.

Keywords: carbohydrates; chemoselectivity; dehydrations; glycosylations; oligosaccharides.