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An Optically Active D-Aldopentose a Produced an Optically Active Alditol

Question 27

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An optically active D-aldopentose A produced an optically active alditol B upon treatment with sodium borohydride.When this aldopentose was subjected to a Ruff degradation,a D-aldotetrose C was generated.This aldotetrose yielded an optically inactive aldaric acid D upon oxidation with nitric acid.Use these data to provide the structures of compounds A,B,C,and D.

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