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De novo synthesis of a differentially protected mannose: a) d-proline, DMF; b) MgBr2·Et2O, CH2Cl2; c) AcCl, BnOH, 110°C; d) PhOCSCl, pyridine, CH2Cl2; e) Bu3SnH, AIBN, toluene, 120°C; f) Dess–Martin periodinane, CH2Cl2, 0°C; g) MgBr2·Et2O, CH3MgBr, CH2Cl2; h) H2, Pd/C, EtOAc; Cl3CCN, Cs2CO3, CH2Cl2; i) l-proline, DMF. AIBN=2,2′-azobisisobutyronitrile.
