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. Author manuscript; available in PMC: 2012 Nov 23.
Published in final edited form as: J Am Chem Soc. 2011 Nov 1;133(46):18975–18991. doi: 10.1021/ja208390n

Scheme 1.

Scheme 1

Synthesis of bisecting GlcNAc- and LacNAc-containing N-glycan oxazolines a

aReagents and conditions: (a) BSP, TTBP, Tf2O, CH2Cl2, 56%. (b) 80% aq. AcOH, 80%. (c) TBDMSCl, pyridine, 95%. (d) BF3·OEt2, CH2Cl2, 76%. (e) TFA, CH2Cl2, 88%. (f) TMSOTf, CH2Cl2, 54%. (g) 1) NH2NH2 monohydrate, EtOH, H2O; 2) Ac2O, pyridine, 77% (2 steps). (h) 1) Pd(OH)2-C, H2, CH2Cl2, MeOH; 2) Ac2O, pyridine, 89% (2 steps). (i) TMSBr, BF3·OEt2, 2,4,6-collidine, CH2Cl2, 48%. (j) MeONa, MeOH, quantitative. (k) MeONa, MeOH, quantitative. (l) DMC, Et3N, H2O, quantitative. (m) UDP-Gal, β-1,4-galactosyltransferase, buffer, quantitative. (n) DMC, Et3N, H2O, quantitative.