Efficient Synthesis of Anticoagulant Fondaparinux via Orthogonal One-Pot Glycosylation and Microwave-Assisted Simultaneous O,N-Sulfonation
Qingqing Shi , Pengchao Liu , Biao Yu , Peng Xu
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (18) : 2325 -2330.
Efficient Synthesis of Anticoagulant Fondaparinux via Orthogonal One-Pot Glycosylation and Microwave-Assisted Simultaneous O,N-Sulfonation
Here, we report an effective approach to the synthesis of anticoagulant fondaparinux, utilizing orthogonal one-pot [1+2+2] glycosylation, simultaneous O,N-sulfation and global debenzylation at atmospheric pressure as key steps. The synthetic route was achieved through the longest linear sequence of 12 steps with 19% overall yield from a commercially available disaccharide. The present synthetic route remarkably enhances synthetic efficiency and streamlines the purification process, thereby opening up a new avenue for the large-scale synthesis of fondaparinux and relevant heparin fragments.
Fondaparinux / One-pot glycosylation / O,N-Sulfation / Global debenzylation / Carbohydrates / Glycosylation / Synthetic methods
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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