Skip to main content
. 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 2.

Scheme 2

Preparation of building blocks for the GPI anchor carbohydrate moiety of T. brucei. Reagents and conditions: a) MeONa, MeOH, rt, 1 h, then p-TSA, MeOH, rt, 18 h; then acetic anhydride, pyridine, rt, 3 h, 73% (for 3 steps) then TiCl4, Et3SiH, DCM, 0 °C, 8 h, 83%; b) m-CPBA, DCM, −15 °C, 30 min, 96%; c) NaOMe, MeOH, rt, 1 h, then TBDPSCl, Imidazole, DMF, 0 °C, 2 h, 98%; d) BnBr, NaH, DMF, 0 °C, 1 h, 75%; e) HF-pyridine in pyridine, rt, 18 h, 61%; f) NaH, NapBr, DMF, 0 °C, 5 h, 95%; g) m-CPBA, DCM, −15 °C, 30 min, 72%; h) Pb(AcO)4, 1-aminobenzotriazole, DCM, −78 °C, 1 h, 95%; i)NH2NH2-AcOH, DMF, 50 °C, 4 h; then 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride, DBU, DCM, rt, 1 h, 71%.