Ethers, benzyl, of sugars

More successful applications of periodate oxidation to substituted sugars were made employing the sugar phosphates and phosphoric acids,63 66 the chloraloses, 62 70 the benzyl ethers of sugars,71 72 a dimethyleneoxy sugar,73... 

Benzyl ethers.2 Benzyl ethers of sugar alcohols can be obtained in 82-98% isolated yield by reaction with 1 and catalytic amounts of triflic acid under these conditions isopropylidene and benzylidene acetal groups are stable, as well as ester and imide groups. The reagent thus is comparable to benzyl triflate (6,44). 

Maher, George G., The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose, X, 257-272 Maher, George G., The Methyl Ethers of D-Galactose, X, 273-282 Manners, D. J., The Molecular Structure of Glycogens, XII, 261-298 Marsh, C. A. See Conchie, J. McCloskey, ChesterM., Benzyl Ethers of Sugars, XII, 137-156 McColloch, R. J. See Kertesz, Z. I. McDonald, Emma J., The Polyfructo-... 

Table of Benzyl Ethers of Sugars and Some of Their Derivatives. 154... 

The benzyl ethers of sugars comprise one of the important classes of derivatives employed in sugar chemistry. These compounds are of value synthetically because the benzyl group can be readily removed under mild conditions by hydrogenolysis according to the following reaction. 

Three methods have been utilized successfully in the preparation of benzyl ethers of sugars. 

Palladium is the favored catalyst, although Raney nickel has been found satisfactory for the hydrogenolysis of benzyl ethers of sugars. Copper chromite has been successfully employed in other systems. ... 

The benzyl ethers of sugars and their derivatives are often crystalline compounds, and many can be distilled. Table III gives some physical properties of some benzyl ethers of sugars and of some of their derivatives. 

McCloskey, Chester M., Benzyl Ethers of Sugars, 12, 137-156 McColloch, R. j. See Kertesz, Z. I. McDonald, Emma J., The Polyfructosans and Difruotose Anhydrides, 2, 253-277... 

In early work it was reported that benzyl ethers of sugars can be cleaved by hydrogenolysis with sodium amalgam or by catalytic hydrogenolysis using platinum metals in acetic acid.224 This also applies to anomeric benzyl glycosides. Acetic acid is still the recommended solvent, but the customary catalyst is palladium... 

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