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. 2022 Dec 2;13:7438. doi: 10.1038/s41467-022-34788-3

Fig. 2. Chemical synthesis of the unnatural donor, UDP-4-SH-GlcNAc 12.

Fig. 2

Reagents and conditions: a) benzyl alcohol, ytterbium(III) trifluoromethanesulfonate, dichloromethane (DCM), reflux 10 h, to form intermediate 2; b) sodium methoxide (NaOMe), methanol (MeOH), room temperature (RT) 12 h, to form intermediate 3; c) Benzoyl chloride, pyridine (Py), -40°C 8 h, 71% for three steps; d) trifluoromethanesulfonic anhydride, Py, -10 °C, to form reactive intermediate 5; e) potassium thioacetate, dimethylformamide, RT, 64% for two steps; f) FeCl3, DCM, RT, to form reactive intermediate 7; g) tetrabenzyl pyrophosphate, lithium diisopropylamide, tetrahydrofuran, -78°C, 66% for two steps; h) Pd/C, H2, MeOH, room temperature, to form reactive intermediate 9; j) UMP-morpholidate, Tetrazole, Py, room temperature 3 d, 41% for two steps; k) NaOMe, MeOH, RT; l) O2, RT, 3 days, 52% for two steps; m) dithiothreitol in H2O, room temperature, 92%. Experimental details are in the Supplementary Information and the analytical data is in Supplementary Fig. 1–37. The reactive intermediate 5, 7, and 9 were used in the next step without purification (structures of intermediates 2, 3, 5, 7 and 9 in Supplementary Fig. 1).