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By Marcel Florkin; Elmer H Stotz
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Sample text
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.
In the D-series of sugars the IX-hydroxyl is written on the right of the sugar chain in the cyclic form of the Fischer formulae and trans to the CHzOH in the Haworth formulae. It is necessary to relate the pentopyranoses to the hexoses to determine whether the anomeric hydroxyl H-C-OH H-~~ HO-C-~· I I I 0 H-y-OH HC-I CHpH a-D-Glucose HO-C-H ~{-H I ·~-C-OH 0 I IHO-y-H CH I CHpH a-L-Glucose rO~H H~ OH fi-D-Glucose * For clarity the hydrogens are omitted in the Haworth References p. icose formul~.
B) Glycosides (i) Synthetic glycosides Brief mention has already been made of glycosides, the non-reducing hemiacetal derivatives formed by reaction of a monosaccharide with alcohol in the presence of an acid catalyst. These derivatives are relatively stable cyclic compounds which do not mutarotate in aqueous solution. They have in fact lost the properties associated with the carbonyl group and do not undergo reduction or oxidation at C-I (or C-2). When formed by reaction with dry methanolic hydrogen chloride at room temperature the methyl glycosides have a high proportion of the furanose ring structure (furanoside), whereas reaction at elevated temperature results mainly in a pyranose ring (pyranoside).