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. Author manuscript; available in PMC: 2014 May 17.
Published in final edited form as: J Org Chem. 2013 Apr 30;78(10):4730–4743. doi: 10.1021/jo400192e

Scheme 4. 2-Hydroxylamino-2-Deoxyglucose Synthesis.

Scheme 4

a) TES-Cl (12 equiv), DIEA (15 equiv), DMF, 70°C; b) p-anisaldehyde, PPTS, toluene, reflux; c) mCPBA, aq. NaHCO3, DCM; d) TFA:H2O (4:1); e) yeast hexokinase, ATP, MgCl2, citric acid•H2O, pH 8.0; f) cat. CSA, MeOH; g) POCl3, 2,6-lutidine, then TFA/H2O (4:1).