Amino Derivatives of the Gulono-l,4-lactones

Several 2-amino-2-deoxy-D-gulononitrile derivatives (68) have been obtained by treating D-xylose with hydrogen cyanide and an amine. Among the amines that were used in preparing these derivatives were aniline,107-109 9-aminofluorene,110 p-methylphenylamine,109 and benzylamine.109 In all cases, as expected, both the D- and L-gly-cero configurations at C-2 are formed. When a solution of 68 (R = Ph) 

On treatment of 2,3 4,5-di-0-isopropylidene-D-xylose with cyclohexyl isonitrile and ammonium acetate, 2-acetamido-N-cyclohexyl-2-deoxy-3,4 5,6-di-0-isopropylidene-D-gulonamide was formed112 it was reported that only one isomer was produced in this reaction. 

A variety of miscellaneous derivatives of gulonolactone has been reported. Linn treated D-glucofuranurono-6,3-lactone (7) with chlorobenzene and aluminum trichloride in order to obtain115 6-deoxy-6,6-diphenyl-L-gulonic acid (70). Various related compounds were also prepared. When 7 was treated with sulfur dioxide and 2-(isonicotin-oyl)hydrazine in water, 6-deoxy-6-(2-isonicotinoylhydrazino)-6-sulfo-D-gulono-1,4-lactone (71) was formed in 81% yield.116,117 Kawabata 

When 2-4-0-ethylidene-D-glucofuranurono-6,3-lactone [obtained by the hydrolysis of thioacetal 61 (Ph = Et)] was treated with 5,5-dimethyl-l,3-cyclohexanedione (dimedone), 6-deoxy-6,6-bis(4,4-di-methyl-2,6-dioxocyclohexyl)-3,5-0-ethylidene-L-gulono-1,4-lactone (73) was formed in 71% yield.99 

Methyl 2-O-methyl-L-gulonate has been erroneously reported.121 

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