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. 2010 Sep 17;107(40):17107–17112. doi: 10.1073/pnas.1002717107

Scheme 2.

Scheme 2.

(A) Synthesis of nonself glycosyl donor building blocks. Reagents and conditions: (i) Ac2O, Pyr then PhSH, BF3•OEt2, DCM then NaOMe, MeOH then NaH, BnBr, DMF. (B) Synthesis of nonself tetrasaccharides with (B) and without (A) linker group glycoconjugate synthesis. Reagents and conditions: (ii) DMTST, TTBP, DCM, 4 Å mol sieves, -78 °C → RT; (iii) NaOMe, MeOH: (iv) DMTST, TTBP, DCM, 4 Å mol sieves, -78 °C → RT; (v) AcOH, H2O, 50 °C; (vi) Pd/C, H2, MeOH,; (vii) TfN3, NH4HCO3, CuCl2, DCM, H2O. (C) Glycoconjugate synthesis. Reagents and conditions: (viii) alkynyl N-hydroxysuccinimide ester (HCC(CH2)2CO2-NHS), 15% DMSO, TRIS buffer pH 7.0; (ix) aminoguanidine, CuSO4, tris(3-hydroxypropyltrazolylmethyl)amine, sodium ascorbate, PBS (0.1 M, pH 7.0).