Sulfonic Esters of Carbohydrates

Abstract

Publisher Summary This chapter discusses sulfonic esters of carbohydrates. Of the various ways in which sulfonic esters may be synthesized, only two––the use of metallic salts of sulfonic acids and the use of suljonyl halides–– have so far achieved importance in carbohydrate chemistry. Certain sulfonic esters of sugars and sugar alcohols may be employed for hydroxyalkylation. In purifying, and assessing the purity of, sulfonic esters of sugars, knowledge of some of their general physical properties is helpful. Many sulfonic esters of monosaccharides and their derivatives crystallize with comparative ease, thereby affording a means of purification. A few sulfonic esters of sugars have been purified chromatographically. Crystalline sulfonic esters of monosaccharides and their derivatives are colorless, and exhibit sharp melting points. Sulfonic esters of sugar alcohols often react similarly with ammonia; thus, 1,4:3,6-dianhydro-2,5-di-O-tosyl-D-manniatnold -sorbitol give the corresponding 2,5-diamino-2,5-dideoxy derivatives.