Furanose derivatives oxidation with

D-glucose and its lactone from 2,3,6-trimethyl-D-glucose provided conclusive proof that the ring system was not of the hexylene oxide type.142 188 The final evidence necessary to characterize the tetramethylglucose in question as a furanose derivative was provided by Haworth, Hirst and Miller,176 who demonstrated that oxidation of the tetramethylglucose with bromine water and of the resulting lactone with nitric acid yielded dimethoxysuccinic acid and oxalic acid, but not i-zyZo-trimethoxyglutaric acid, the absence of which ruled out a pyranose structure. 

Further chemistry with the methoxylated products leads to the facile production of polycyclic molecules. Methoxylation of more substituted substrates is well covered in the review by Moeller [34], who has also described a number of reactions where the cation radical generated by the oxidation of an olefin is trapped by an alcohol group in an intramolecular reaction [35-37] to form a cyclic product. Recently, Moeller has applied such reactions to the synthesis of sugar derivatives an illustrative example is the oxidation of tetramethoxy-furanose derivative ... 

Derivatives of aldoses in which the terminal aldehyde function is oxidized to a car boxylic acid are called aldonic acids Aldonic acids are named by replacing the ose ending of the aldose by omc acid Oxidation of aldoses with bromine is the most com monly used method for the preparation of aldonic acids and involves the furanose or pyranose form of the carbohydrate... 

The diacetamide compounds were regularly obtained in all degradations employing ammonia with or without silver oxide until Hockett and Chandler applied the method to hexaacetyl-D-gluco-D-flruZo-heptono-nitrile (XLIX) and obtained a monoacetamide derivative that was identified as iV-acetyl-D-glucofuranosylamine (L). The furanose structure of L was established by lead tetraacetate oxidation. They... 

Piperidones of two types have been prepared from saccharide derivatives. Those of one type are lactams, exemplified by 187, obtained by oxidizing255 5-azido-5-deoxy-2,3-0-isopropyidene-/3-D-ribo-furanose (185) to 186, reducing the lactone 186 to the amine, and cyclizing this to 187. The other type comprises the 4-piperidones such as 189 this is obtained256 by oxidizing methyl a-D-arabinopyrano-side (188) with periodate, and treating the product with methylamine and 3-oxopentanedioic acid the bicyclic compound obtained from the a-glycoside differs from that from the /3 anomer. 

The oxidation of 1,2-O-isopropylidene-D-glucofuranose with lead tetraacetate was found by Criegee to yield formaldehyde,43 which confirmed the presence of a furanose ring in the sugar derivative. The major oxidation fragment, l,2-0-isopropylidene-5-oZde/q/do-D-a yZo-pentodialdose, was characterized subsequently by Iwadare,88 and has recently been shown to crys-... 

Oxidation of the monoacetone derivative, 2,3-isopropylidene-L-sorbose (XLIX), with air in the presence of platinum has reportedly given L-gulo-saccharoascorbic acid (LI), after treatment of the unstable intermediate 2,3-isopropylidene-2,5-furanose-L-gulosaccharic acid (L) with hydrochloric acid. 109... 

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