TY - JOUR A1 - Dahlqvist, Alexander A1 - Furevi, Axel A1 - Warlin, Niklas A1 - Leffler, Hakon A1 - Nilsson, Ulf J. T1 - Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 1046 EP - 1060 SN - 1860-5397 DO - 10.3762/bjoc.15.102 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.102 KW - C-galactoside KW - galectin-1 KW - hydroboration KW - inhibition KW - selective KW - triazole N2 - Galectins are carbohydrate recognition proteins that bind carbohydrates containing galactose and are involved in cell signaling and cellular interactions, involving them in several diseases. We present the synthesis of (aryltriazolyl)methyl galactopyranoside galectin inhibitors using a highly diastereoselective hydroboration of C1-exo-methylene pyranosides giving inhibitors with fourfold or better selectivity for galectin-1 over galectin-3, -4C (C-terminal CRD), -4N (N-terminal CRD), -7, -8C, -8N, -9C, and -9N and dissociation constants down to 170 µM. ER -