Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 7. Conversion of thiocarbonates into deoxy-sugars

Abstract

Radical-initiated reduction of five- or six-membered ring thiocarbonates, followed by alkaline hydrolysis, affords a convenient synthesis of 2-, 3-, 4-, and 5-deoxy-sugars. For 5,6- and 4,6-thiocarbonates the regiospecificity of the reaction complements the recently developed synthesis of 6-deoxy-sugars by ring opening of the same thiocarbonates with methyl iodide. Applications in the synthesis of 2-deoxy-D-ribose and 2′-deoxyadenosine are described.