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. Author manuscript; available in PMC: 2016 Sep 7.
Published in final edited form as: Chemistry. 2015 Aug 6;21(37):12920–12926. doi: 10.1002/chem.201501844

Scheme 3.

Scheme 3

The assembly of the GPI anchor moiety of T. brucei. Reagents and conditions: a) NIS, TfOH, DCM, −25 °C, 30 min, 89%; b) DDQ, DCM: H2O = 10: 1, rt, 2 h, 17: 82%; 20: 77%; c) Tf2O, TMB, DTBMP −40 °C to rt then 10% TFA in DCM, rt, 1 h; (18: 87%, α only; 21: 67%, α-only); d) TfOH, DCM, −25 °C to rt, 3 h, 71%, α:β > 20:1; e) TfOH, DTBMP, DCM, −60 °C to rt, 18 h, then 10% TFA in DCM, rt, 1 h, 76%, α-only; f) Ac2O, pyridine, DMAP, rt, 4 h; g) NH2NH2-AcOH, pyridine, rt, 1 h; h) TMSOTf, DCM, −25 °C to rt, 1 h, 51% over three steps; i) H2, Pd/C, AcOH, MeOH, rt, 24 h, then MeONa, MeOH, rt, 1 h, 65%.