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An Optically Active D-Aldopentose Produced an Optically Inactive Aldaric Acid

Question 94

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An optically active D-aldopentose produced an optically inactive aldaric acid upon treatment with HNO3. When this aldopentose was subjected to a Ruff degradation, a D-aldotetrose was generated. This aldotetrose gave an optically inactive alditol upon reduction with NaBH4. Use these data to provide the structure of the starting D-aldopentose.

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