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. Author manuscript; available in PMC: 2016 Apr 18.
Published in final edited form as: J Carbohydr Chem. 2013 Sep 2;32(5-6):392–409. doi: 10.1080/07328303.2013.815196

Scheme 3.

Scheme 3

Reagents and Conditions: i) 2 eq BnOH, 3 eq BF3OEt2, CH2Cl2, 79%; ii) 0.3 M NaOMe, MeOH/CH2Cl2, −10°C; iii) PhCH(OMe)2, 0.08 eq camphorsulfonic acid, CH3CN, 77%; iv) 2 eq Tf2O, 5 eq pyridine, −20°C to 10°C; 6 eq tetrabutylammonium acetate, toluene, 60°C%; v) 6 eq DAST, CH2Cl2, −5°C to rt; vi) 6 eq AcCl, MeOH/CH2Cl2, 28% yield from 18; vii) H2N(CH2)2NH2, nBuOH, 90°C; acetic anhydride, pyridine rt, 80%; viii) H2, Pd/C, MeOH; acetic anhydride, pyridine, rt, 60%.