C. Glaudemans, H. G. Fletcher
1972
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Abstract
Publisher Summary This chapter discusses the preparation of a partially benzylated aldopyranose by the synthesis of 2,3,4,6-tetra-O-benzyl-α- d -glucopyranose. While it has also been made from other glucopyranosides, commercial availability and inexpensiveness makes methyl α- d -glucopyranoside the starting material of choice. In preparation, methyl α- d -glucopyranoside is suspended in 150 ml of dry dioxane with 250 g of powdered potassium hydroxide, and the mixture is stirred and gently boiled under a reflux condenser while 318 ml of benzyl chloride is added in dropwise fashion over a period of ∼ 40 min. The residue is cooled and sufficient water is added to dissolve the crystalline mass, the methyl 2,3,4,6-tetra-O-benzyl-α- d -glucopyranoside then being extracted with ether.