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. Author manuscript; available in PMC: 2014 Nov 15.
Published in final edited form as: J Org Chem. 2013 Nov 5;78(22):11525–11534. doi: 10.1021/jo402118j

Scheme 2. Synthesis of Oligosaccharide Donorsa.

Scheme 2

aReagents and conditions: (a) H2-activated [Ir(COD)(PMePh2)2]PF6, THF, 23°C; 6, NIS/TfOH, MeCN, 23 °C; NaOMe, 78%; (b) TESOTf, CH2Cl2, 0->23 °C, 88%; (c) H2-activated [Ir(COD)(PMePh2)2]PF6, THF, 23 °C; 9, NIS/TfOH, MeCN, 23 °C, 71%; (d) H2-activated [Ir(COD)(PMePh2)2]PF6, THF, 23 °C; 7, NIS/TfOH, MeCN, 23 °C, 76% for 13a, 69% for 13b, 83% for 13c; (e) NaOMe, MeOH, 23 °C; TFA/H2O (4:1); Ac2O, TEA, DMAP, CH2Cl2, 23 °C; (f) H2-activated [Ir(COD)(PMePh2)2]PF6, THF, 23 °C; NIS/H2O, 23 °C; (g) Cs2CO3, Cl3CCN, CH2Cl2, 23 °C, 78% for 4a, 85% for 4b, 73% for 4c.