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. 2020 Apr 14;63(10):5442–5457. doi: 10.1021/acs.jmedchem.0c00215

Scheme 2. Synthesis of Epimeric Ligands with a Phosphate Group at the Anomeric Carbon: α-d-Glucopyranosyl 1,3,4-Trisphosphate (6) and β-d-Glucopyranosyl 1,3,4-Trisphosphate (7).

Scheme 2

Reagents and conditions: (a) MeOH, cat. PdCl2, 6 h; (b) (1) DCM, 5-phenyl-1H-tetrazole, (BnO)2PN(iPr)2, 20 h and (2) mCPBA, −78 °C to room temperature; (c) MeOH/H2O (10:1 v/v), cat. Pd(OH)2/C, H2, NaHCO3, 24 h.