1: α-D-Glucopyranosyl azide; 2-(diphenylphosphanyl)phenyl pentanoate in N,N-dimethyl acetamide T=70°C; Staudinger reduction-acetylation; 18 h; 2: With water in N,N-dimethyl acetamide T=70°C; 2 h; 3: acetic anhydride Further stages.;

1: α-D-Glucopyranosyl azide; 2-(diphenylphosphanyl)phenyl pentanoate in N,N-dimethyl acetamide T=70°C; Staudinger reduction-acetylation; 18 h; 2: With water in N,N-dimethyl acetamide T=70°C; 2 h; 3: acetic anhydride Further stages.;

1: α-D-Glucopyranosyl azide; 2-(diphenylphosphanyl)phenyl pentanoate in N,N-dimethyl acetamide T=70°C; Staudinger reduction-acetylation; 18 h; 2: With water in N,N-dimethyl acetamide T=70°C; 2 h; 3: acetic anhydride Further stages.;

1: α-D-Glucopyranosyl azide; 2-(diphenylphosphanyl)phenyl pentanoate in N,N-dimethyl acetamide T=70°C; Staudinger reduction-acetylation; 18 h; 2: With water in N,N-dimethyl acetamide T=70°C; 2 h; 3: acetic anhydride Further stages.;

triethylamine in dichloromethane T=20°C; 1 h;

1: 77 percent / HCl / methanol / 1 h / 20 °C 2: 96 percent / triethylamine / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: n-BuLi; TMEDA / hexane / 1.5 h / 20 °C 1.2: 61 percent / hexane / 16 h / 20 °C 2.1: 77 percent / HCl / methanol / 1 h / 20 °C 3.1: 96 percent / triethylamine / CH2Cl2 / 1 h / 20 °C View Scheme

1.1: 74 percent / NaH / dimethylformamide; various solvent(s) / 0 - 20 °C 2.1: n-BuLi; TMEDA / hexane / 1.5 h / 20 °C 2.2: 61 percent / hexane / 16 h / 20 °C 3.1: 77 percent / HCl / methanol / 1 h / 20 °C 4.1: 96 percent / triethylamine / CH2Cl2 / 1 h / 20 °C View Scheme