Ca2+-Mediated Regioselective Functionalization of Unprotected Mannopyranosides
Year: 2026
Type: article
Abstract: Regioselective functionalization of unprotected monosaccharides is a long-standing challenge in synthetic organic chemistry. Recent methodological developments have established transient covalent adduction and organocatalytic approaches leveraging non-covalent interactions as potential solutions to this synthetic problem. In contrast, strategies employing biomimetic metal cation chelation as a mechanism for achieving substrate selectivity and regioselectivity have been comparatively underexplored. Herein, we report a Ca2+-mediated regioselective acylation reaction of unprotected mannopyranosides. By leveraging a CaCl2/collidine system, we were able to achieve the facile generation of C2 monofunctionalized mannopyranoside products in appreciable yields and high regioselectivity. A gram scale synthesis of C2-acetylated methyl α-D-mannopyranoside expedited access to key synthetic intermediates, thereby demonstrating the practical utility of this methodology.
Source: Synthesis
DOI: 10.1055/a-2945-4052
Institution: Vanderbilt University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
OpenAlex ID: W7204461456