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. 2005 Dec 22;103(1):15–20. doi: 10.1073/pnas.0509693102

Fig. 3.

Fig. 3.

Synthesis of truncated Globo H sequences. (A) One-pot synthesis of Globo H tetrasaccharide analogs 3a and 3b. (i) NIS, TfOH, –50°C. (ii) NIS, TfOH, –20°C, 42% from 10. (iii) a) Zn, AcOH; b) Ac2O, Py; c) NaOMe; d) H2, Pd-black, 69% over four steps. (iv) TfN3, CuSO4, 64%. (B) One-pot synthesis of Globo H trisaccharide analogs 2a and 2b. (i) NIS, TfOH, –50°C. (ii) NIS, TfOH, –20°C, 54% from 10. (iii) a) Zn, AcOH; b) Ac2O, Py; c) NaOMe; d) H2, Pd-black, 66% over four steps. (iv) TfN3, CuSO4, 89%. (C) Synthesis of Globo H disaccharide analogs 1a and 1b. (i) NIS, TfOH, –20°C, 60% (α:β = 2:1). (ii) H2, Pd-black, 59%. (iii) TfN3, CuSO4, 52%.