1: HCl / 2 h / 20 °C 2: pyridine / 8 h / 20 °C 3: 15 g / AcOH; H2SO4 / 0 - 20 °C View Scheme

1: HCl / 2 h / 20 °C 2: pyridine / 8 h / 20 °C 3: 15 g / AcOH; H2SO4 / 0 - 20 °C View Scheme

ammonia Product distribution / selectivity;

1: L-ribofuranose With hydrogenchloride in methanol T=20°C; Acetylation; 3 h; 2: acetic anhydride With pyridine T=20°C; Acetylation; 24 h; 3: acetic anhydride With sulfuric acid; acetic acid T=20°C; Acetylation; 14 h; Further stages.;

1.1: sulfuric acid / 3 h / 20 °C 2.1: lithium carbonate / 0.5 h / 20 °C 2.2: 5 h / 30 - 100 °C 3.1: sulfuric acid / 1 h / 20 - 25 °C 3.2: 3 h / 20 °C View Scheme

1: conc. sulfuric acid / 2 h / 20 °C 2: 85 percent / sodium hydride / dimethylformamide / 12 h / 20 °C 3: 1M hydrogen chloride / acetic acid; H2O / 2 h / 100 °C 4: 87 percent / sodium borohydride / ethanol / 1 h / 50 °C View Scheme

2: 88 percent / H2 / Raney Ni / methanol 3: 1.) imidazole, 2.) NaH / DMF 4: 70 percent / NaBH4 / ethanol 5: 88 percent / (COCl)2, DMSO, Et3N / CH2Cl2 6: Ph3P, DEAD / dimethylformamide 8: 99 percent / RuO4 / CH2Cl2; CCl4 9: NaH / 1,2-dimethoxy-ethane 10: 1.) p-TSOH, AC2O, 2.) K2CO3 / 2.) benzene 11: 80 percent / pyridine / 38 °C 12: 1.) CH3CH=C(CH3)2, NaOCl2-NaH2PO4, 2.) (i-Pr)2NEt / 1.) t-BuOH, H2O; 2.) CH2Cl2 13: 75 percent / NaBH4 / tetrahydrofuran; various solvent(s) View Scheme