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. Author manuscript; available in PMC: 2014 Mar 27.
Published in final edited form as: J Am Chem Soc. 2013 Mar 19;135(12):4700–4703. doi: 10.1021/ja401385v

Scheme 3. Synthesis of Protected Tetradecasaccharide 18a.

Scheme 3

aReagents and Conditions: (a) 5, NIS, AgOTf, CH2Cl2, 4Å MS, −50 to − 20 °C, 1.25 h, 91%; (b) BH3·THF, n-Bu2BOTf, CH2Cl2, 0 °C, 4 h, 99%; (c) 15, NIS, AgOTf, CH2Cl2, −10 °C, 2 h, 87%; (d) NaOMe, MeOH/THF, rt, 1.7 h, 93%; (e) 9, Cp2Zr(OTf)2·THF, CH2Cl2, 0 °C, 1.5 h, 71%.