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By Hassan Saad El Khadem

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Extra resources for Carbohydrate chemistry: monosaccharides and their oligomers

Sample text

C y c l i c Structures, Ring S i z e , a n d A n o m e r i c Configuration 37 conformation (see page 45). Then, by using selective decoupling tech­ niques to identify the other protons, it is possible to determine their orientation relative to one another. The Ή - N M R spectrum of a solution of α-D-glucopyranose was shown in Fig. 5. Because multinuclear magnetic resonance spectrometers having Fourier transform capabilities are now readily available, it is customary to 13 confirm the Ή - N M R results with natural-abundance C-nuclear magnetic resonance spectroscopic measurements.

Is oxidized twice). By ascertaining the outcome of the oxidation, it is possible to determine the number and 41 Ml. C y c l i c Structures, Ring S i z e , a n d A n o m e r i c Configuration Periodate oxidation of the possible methyl a-D-glucosides CHgOH HO-(j-H HO-C-H H-C-Oj/ >^ 0 Me OMe CHgOH ' 3 moles of I 0 4 consumed (+ 2 HCOOH + HCHO) 2 moles of I 0 4 consumed (+ HCOOH + HCHO) CHgOH CH20H HO-C-H ^ 0 OMe . 1 I OH r 2 moles of I 0 4 consumed (+ HCHO) oh 2 moles of I 0 4 consumed (+ HCOOH) 0 OMe 3 moles of I 0 4 consumed (+ 2 HCOOH) type (primary or secondary) of adjacent hydroxyl groups present in a molecule.

Note that this is a much more selective reaction than anomerization. The anomeric effect has been interpreted in terms of polar interactions between the negative group attached to the anomeric position (for exam­ ple, the halogen atom of a glycosyl halide) and the nonbonded electron pair of the ring oxygen. Newman projections will reveal that an equatorially oriented halogen will be gauche to both electron lobes of the ring oxygen, whereas an axially oriented halogen will be gauche to only one lobe and antiperiplanar to the other.

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