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. 2014 Sep 25;57(19):8056–8071. doi: 10.1021/jm500946r

Scheme 6. Synthesis of αGlcN(1↔1)αMan-Based Lipid A Mimetics (α,α-GM-LAMs) 1–3.

Scheme 6

Reagents and conditions: (a) aq. 50% NH2OH, THF, 0 °C: 46 (53%), 47 (2%), 48 (9%), recovered 36 (15%); (b) 49, DIC, DMAP, CH2Cl2, 0 °C, 83%; (c) DBU, CH2Cl2; (d) 50, EDC, CHCl3; (e) HF·Py, THF; (f) →57 + 59, DIC, DMAP, 50, CH2Cl2, 0 °C; (g) →58 + 60, DIC, DMAP, 51, CH2Cl2, 0°C; (h) 1. (BnO)2PN(iPr)2, 1H-tetrazole, CH2Cl2, 2) mCPBA, −78 °C, 91% for 61, 89% for 62; (i) Pd black, toluene–MeOH, 1:1, 72% for 1, 87% for 2, 81% for 3.