Fig. 2: Synthesis of glucosamine monosaccharide building blocks 6, 7, 8, and 9. | Nature Communications

Fig. 2: Synthesis of glucosamine monosaccharide building blocks 6, 7, 8, and 9.

From: Poly-β-D-(1,6)-N-acetyl-glucosamine (PNAG) glycan vaccines with broad spectrum neutralizing activities

Fig. 2

Reagents and conditions: (a) NaOMe, phthalic anhydride, MeOH, 65 °C, 2 h; (b) Ac2O, pyridine, RT, o/n, 73% (two steps); (c) TolSH, BF3O·Et2O, CH2Cl2, RT, 24 h, 65%; (d) NaOMe, MeOH, RT, 2 h; (e) TrCl, cat. DMAP, pyridine, 50 °C, o/n, 95%, (two steps); (f) BzCl, cat. DMAP, pyridine, RT, o/n, 88%; (g) pTSA, MeOH/CH2Cl2, RT, 8 h, 91%; (h) Ac2O, pyridine, RT, 2 h, 99%; i HOPO(OBu)2, NIS/TfOH, CH2Cl2, MS 4 Å, 0 °C, o/n, 95%; (j) HO(CH2)5N3, TMSOTf, CH2Cl2, MS 4 Å, −40 to −25 °C, 2 h, 90%; and (k) AcCl, CH2Cl2/MeOH, RT, o/n, 97%. Phth Phthalimide, Tr Trityl, DMAP 4-(Dimethylamino)pyridine, pTSA p-Toluenesulfonic acid monohydrate, NIS N-Iodosuccinimide.

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