Abstract
Publisher Summary This chapter presents a review of the synthesis, reactions, and related derivative of the gulono-1,4-lactones. The most efficient synthesis of L -gulono-1,4-lactone entails the reduction of D -glucofuranurono-6,3-lactone, which can be obtained from D -glucose. D -Gulose has also been prepared by the oxidation of 4,6- O -ethylidene-l, 2- O -isopropylidene-α- D -galactopyranose, followed by reduction and hydrolysis. The addition of hydrogen cyanide to D -xylose resulted in the formation of cyanohydrins which on hydrolysis, afforded a mixture of D -gulonic acid and D -idonic acid. It has also been reported that D -galactose can be isomerized with molybdic acid to a mixture containing D -talose and D -gulose, but the yields are low. A number of derivatives of gulono-1,4-lactone have been prepared that, by reduction, would provide selectively protected derivatives of gulose. It is found that when L -gulono-1,4-lactone was treated with benzaldehyde and concentrated sulfuric acid, 2, 6:3, 5-di-O-benzylidene- L -gulono-1,4-lactone is formed. A variety of amino derivatives of L -gulonic acid has also been reported. The miscellaneous derivatives of the gulono-1,4-lactones are also elaborated.
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