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. Author manuscript; available in PMC: 2014 Sep 4.
Published in final edited form as: J Am Chem Soc. 2013 Aug 22;135(35):10.1021/ja405990z. doi: 10.1021/ja405990z

Scheme 3.

Scheme 3

Synthesis of heptasaccharide 18.a

aReagents and conditions: (a) NIS/TMSOTf, MS AW-300, CH2Cl2, 0 °C→r.t., 64%; (b) NaOMe, MeOH, CH2Cl2; (c) H2NCH2CH2NH2, n-BuOH, PhMe, 90 °C; (d) Ac2O, Et3N, MeOH; (e) H2, Pd(OH)2/C, MeOH, H2O, 77% (4 steps); (f) sat. aq. NH4HCO3, 40 °C, quantitative.