Synthesis of the 3 ’ -O-sulfated TF antigen with a TEG-N3 linker for glycodendrimersomes preparation to study lectin binding

Abstract The synthesis of gram quantities of the TF antigen (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) and its 3’-sulfated analogue with a TEG-N3 spacer attached is described. The synthesis of the TF antigen comprises seven steps, from a known N-Troc-protected galactosamine donor, with an overall yield of 31%. Both the spacer (85%) and the galactose moiety (79%) were introduced using thioglycoside donors in NIS/AgOTf-promoted glycosylation reactions. The 3’-sulfate was finally introduced through tin activation in benzene/DMF followed by treatment with a sulfur trioxide–trimethylamine complex in a 66% yield. Beilstein J. Org. Chem. 2024, 20, 173–180. doi:10.3762/bjoc.20.17
Source: Beilstein Journal of Organic Chemistry - Category: Chemistry Authors: Tags: regioselective sulfation thioglycoside donors Thomsen – Friedenreich antigen Full Research Paper Source Type: research