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. 2014 Jan 17;19(1):1120–1149. doi: 10.3390/molecules19011120

Scheme 1.

Preparation of the cyclic sulfate intermediate 5.

Scheme 1

Reagents and conditions: (a) 2-bromoethanol, BF3·OEt2, CH2Cl2, 91%; (b) NaN3, DMF, 96%; (c) MeONa, MeOH, 65%; (d) 2,2 dimethoxypropane, APTS, acetone; (e) AcOH, H2O, 85%; (f) SOCl2, NEt3, CH2Cl2; (g) RuCl3, NaIO4, CH2Cl2/CH3CN, 66%.