Reduction of D-sorbose gives sorbitol.

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Chapter 25.SE, Problem 51AP

Interpretation Introduction

Interpretation:

Reduction of D-sorbose gives sorbitol.

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a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D. b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α- glycoside link. Treatment of E with Ag2O and excess Mel gives an octamethyl derivative F. Hydrolysis of F in dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as shown below.) HO OMe OMe MeO MeO MOH OMe mOH OMe OMe

a) The D-aldopentose A, C5H1005, reacts with HNO3 to yield an optically active aldaric acid B. Kiliani-Fischer chain extension of A produces a pair of D-aldohexoses C and D. C is converted by HNO3 to an optically active aldaric acid, but D is converted by HNO3 to an optically inactive aldaric acid. Write acyclic Fischer projections for A, B, C, D.

A D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with NABH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?