Carbohydrates by Marcel Florkin; Elmer H Stotz
By Marcel Florkin; Elmer H Stotz
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28) and sulphate have been introduced into the sugar molecule by this means. The reaction is carried out in anhydrous inert solvent with alcohols or the silver salts of phenols or acids in the presence of silver carbonate or pyridine. The most commonly used acetohalogen compounds are the chloride or bromide (CLXXVI) which exist in the a-form and replacement mostly occurs with Walden inversion and the formation of a fJ-derivative (CLXXVII). :_g" , /:_O_a:_:. ,. _a~" :~2:. P_h_. ~4~1~ OAe (CLXXVI) (CLXXVII) The esters of toluene p-sulphonic acid (tosyl) and methane sulphonic acid (mesyl)88 of special interest because their removal can yield anhydrosugars (p.
C) Determination 01 the ring size in monosaccharides There are several well-established methods for the determination of the ring size, such as oxidative degradation of the methylated sugars and a comparison with the lactones of the sugar acids s6 or oxidation of the glycoside by periodate and characterisation of the products of oxidation s7 • In the former method the free hydroxyl groups of the methyl glycosides are blocked by methyl ether groups. Hydrolysis of the glycosidic methoxyl is followed by hypohalite oxidation.
For this reason sugar acetates should be utilized with caution in structural investigations. The fully substituted derivatives, however, are of considerable value for the preparation of acetohalogenoses87 , derivatives in which the acetoxy radical on the potential reducing group in, for example, p-n-glucose pentaacetate is replaced by a halogen atom. The resulting acetyl glycosyl halides. (CLXXV) are exceedingly valuable in synthetic work because of the ease with which the halogen atom may be replaced.