1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2.5 h / -78 °C / Inert atmosphere View Scheme

1: methyl 4,6-O-benzylidene-2-O-benzyl-α-D-glucopyranoside With sodium hydride in N,N-dimethyl-formamide; mineral oil T=0°C; 0.25 h; Inert atmosphere; 2: benzyl bromide in N,N-dimethyl-formamide; mineral oil T=20°C; 16 h; Inert atmosphere;