Stereoselective Protection-Free Modification of 3-Keto-saccharides
Nittert Marinus1, Nabil Tahiri1, Margherita Duca1
1Stratingh Institute for Chemistry, University of Groningen, Groningen 9747 AG, The Netherlands.
Abstract:
Unprotected 3-keto-saccharides have become readily accessible via site-selective oxidation, but their protection-free functionalization is relatively unexplored. Here we show that protecting groups are obsolete in a variety of stereoselective modifications of our model substrate methyl α-glucopyranoside. This allows the preparation of rare sugars and the installation of click handles and reactive groups. To showcase the applicability of the methodology, maltoheptaose has been converted into a chemical probe, and the rare sugar evalose has been synthesized.
Related Concept Videos
Protecting Groups for Aldehydes and Ketones: Introduction
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Protein Glycosylation
Glycosylation occurs in...
Biosynthesis of Polysaccharides
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...


