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. Author manuscript; available in PMC: 2018 Aug 18.
Published in final edited form as: Angew Chem Int Ed Engl. 2018 May 18;57(30):9268–9273. doi: 10.1002/anie.201803536

Figure 3.

Figure 3

A) The building blocks used for the assembly of the three O-mannosyl scaffold structures. B) Synthetic scheme. Reagents and conditions: a) TMSOTf, DCM, −60°C, 5: 85%; 10: 79%; 14: 75%; 16: 82%; b) i) TFA, DCM; ii) Zn, AcOH; iii) Ac2O, Py, 80% over three steps; c) NIS, AgOTf, DCM/Et2O = 1:1, 0 °C, 7: 93%; 12 : 89%; 18 : 83%; d) i) TFA, DCM; ii) NaOMe, MeOH; iii) FmocOSu, NaHCO3, acetone/H2O = 3:1, 8 : 90%; 13 : 85%; 19 : 87%; e) i) DDQ, DCM/PBS buffer =9:1; ii) Ac2O, Py; iii) EtSH, TsOH, DCM, 9 : 77%; 15 : 81%; f) i) Zn, AcOH; ii) Ac2O, Py, 11: 87%; 17: 82%.