The Gulono-1,4-Lactones A Review of Their Synthesis, Reactions, and Related Derivatives

Add time:07/30/2019    Source:sciencedirect.com

Publisher SummaryThis 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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