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Synthesis of glycotriazolophane 309 by a click reaction. Reagents and conditions: (i) LiOH, H2O, MeOH, THF, 16 h, rt, 93%; (ii) ClCOCOCl, DMF (cat), CH2Cl2, rt, 0.5 h; (iii) 306, DIPEA, 4 Å MS, CH2Cl2, 0 °C, 2 h; (iv) NaOMe, MeOH/CH2Cl2, rt, 3 h, (three steps 37%); (v) 308, CuSO4, sodium ascorbate, MeCN/H2O, rt, 13 h, 56%.
