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Abstract
Hydrolysis of 1,2- O-isopropylidene-3,5-di- O-methyl-α- d-glucofuranose by strong acid yielded 3,5-di- O-methyl- d-glucofuranose ( 6) and its 1,6-anhydride ( 10). The mechanism of the reaction giving 10 is discussed. On treatment with a catalytic amount of sodium methoxide, 1,2,6-tri- O-acetyl-3,5-di- O-methyl- d-glucofuranose ( 8) gives the 6- O-acetyl derivative, whereas complete deacetylation, and subsequent isomerization to the d-fructose derivative 16, takes place in the presence of 0.1 m sodium methoxide. The structure of 16 was proved both chemically and spectroscopically. Reduction of 6 or 8 with a borohydride afforded 3,5-di- O-methyl- d-glucitol. 2 2 According to carbohydrate nomenclature, this may also be named 2,4-di- O-methyl- l-gulitol. To avoid confusion, the alditols are named as d-glucitol derivatives.
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