Abstract
This chapter discusses the formation and removal of benzyl ethers. Benzyl ethers are used as hydroxyl protecting groups in carbohydrate chemistry because they are stable to both acids and bases yet can be removed under mild conditions. Synthesis of carbohydrate benzyl ethers involves treatment of the carbohydrate, in a suitable solvent, successively with base and benzyl halide. The solvents that have been used are N, N -dimethylformamide (DMF), tetrahydrofuran, dioxane, and dimethyl sulfoxide (DMSO). Sodium hydroxide, potassium hydroxide, sodium hydride, silver oxide, and barium oxide have been used as bases and benzyl chloride and benzyl bromide as alkylating reagents. The choice of base is also dependent upon the carbohydrate derivative to be benzylated. If the derivative is base-stable, a strong base such as sodium hydroxide, potassium hydroxide, or sodium hydride is employed.
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