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. Author manuscript; available in PMC: 2022 Nov 19.
Published in final edited form as: ACS Chem Biol. 2021 Sep 27;16(11):2502–2514. doi: 10.1021/acschembio.1c00597

Scheme 3. Synthesis of Disaccharide Oxazolines 30 and 31 Carrying Four or Six Azide Tagsa.

Scheme 3.

a Reagents and conditions: (a) N3(CH2CH2O)2Ts, NaH, DMF, and 0 °C ~ RT; (b) TsOH, MeOH, 60 °C, 20, 72% for two steps, 21, and 54% for two steps; (c) TsO(CH2CH2O)2Ts, NaH, DMF, 0 °C ~ RT, 22, 85%, 23, and 72%; (d) 24, NaH, DMF, 0 °C ~ RT, and 78%; (e) 25, NaH, DMF, 0 °C ~ RT, and 74%; (f) Pd/C, H2, HCl (aq), THF/H2O, then TfN3, K2CO3, CuSO4, CH2Cl2/MeOH/H2O, RT, 28, 67%, 29, and 59%; and (g) DMC, Et3N, H2O, 0 °C, 30, 89%, 31, and 84%.