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. Author manuscript; available in PMC: 2016 Feb 26.
Published in final edited form as: Chemistry. 2014 Oct 29;21(1):305–313. doi: 10.1002/chem.201405424

Scheme 4.

Scheme 4

Synthesis of the family-specific Chlamydia Kdo trisaccharide 31. a) BF3.Et2O, CH2Cl2, mol. sieves 5 Å; b) NIS, AcOH; c) HF-pyridine, CH2Cl2; d) TfOH, CH2Cl2, mol. sieves 3 Å; e) Ac2O, pyr., DMAP; f) lauroyl peroxide, cyclohexane; g) 0.1 M NaOMe, MeOH, then 0.1 M aq. NaOH.