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After a series of Kiliani-Fischer syntheses on D-glyceraldehyde, an unknown sugar was isolated from the reaction mixture. The following experimental data was obtained. What is the structure of this unknown sugar? Data:
- Molecular formula: C6H12O6
- Reacts with phenylhydrazine to give an osazone, mp 178°C.
- Reacts with HNO3 to give an optically active aldaric acid.
- Wohl degradation followed by HNO3 oxidation gives an optically inactive
Aldaric acid.
- Two Wohl degradations followed by HNO3 oxidation give a meso-tartaric acid.
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