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. 2020 Oct 16;63(21):12814–12829. doi: 10.1021/acs.jmedchem.0c01191

Scheme 3. (A) Synthesis of Trisaccharide Alkynylbenzoate Donor 30; (B) Synthesis of Hybrid Trisaccharide Anthracyclines 9–11.

Scheme 3

Reagents and conditions: (a) IDCP, Et2O/DCE (4:1 v/v), then PPh3; (b) NaOMe, MeOH, 78% over two steps (>20:1 α/β); (c) IDCP, Et2O/DCE (4:1 v/v), then PPh3, 100% (>20:1 α/β); (d) (i) NaOMe, MeOH, 85%, (ii) Dess–Martin periodinane, NaHCO3, CH2Cl2, 97%; (e) (i) Ag(II)(hydrogen dipicolinate)2, NaOAc, MeCN/H2O (1:1, v/v), 0 °C, (ii) 20, EDCI·HCl, DIPEA, DMAP, CH2Cl2, 75% over the two steps (1:7 α/β).

Reagents and conditions: (f) (i) 16, PPh3AuNTf2 (10 mol %), DCM, (ii) 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), DCM, pH 7 phosphate buffer (18:1, v/v), 57% over two steps (>20:1 α/β); (g) Pd(PPh3)4, NDMBA, DCM, 81% from 31, 61% for 10; (h) HF·pyridine, pyr., 73% for 9, 73% for 11; (i) aq CH2O, NaBH(OAc)3, EtOH, 52%; (j) 14, PPh3AuNTf2 (10 mol %), DCM, −20 °C, 71% (>20:1 α/β); (k) DDQ, DCM/pH 7 phosphate buffer (18:1, v/v), 90%.