Beyond the two-conformer model: boat conformers provide stereoselectivity in S N 1-type glycosylations of manno -type donors

Chemical Science 2026 Open access

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Authors: Wouter Adriaan Remmerswaal, Daan Hoogers, Joeri Schoenmakers, F. Matthias Bickelhaupt, Thomas Hansen, Jeroen D Codee
DOI: 10.1039/d6sc02312f
Cited by: 1
References: 59

Abstract

While the S N 1 glycosylation reaction mechanism manifold is dominated by addition reactions to half chair oxocarbenium ions we here reveal that mannosyl oxocarbenium ions react on the bottom face of a boat conformer to avoid steric (Pauli) repulsion.

Fields of Study & Subjects

Carbohydrate Chemistry and Synthesis Asymmetric Synthesis and Catalysis Glycosylation and Glycoproteins Research

Publication details

Journal / source
Chemical Science
Publisher
Royal Society of Chemistry (RSC)
Volume
17
Issue
21
Pages
10708–10719
Publication date
1 January 2026
Language
EN