What aldoses are formed when the following aldoses are subjected to the Kiliani-Fischer synthesis: (a) D-threose; (b) D-ribose; (c) D-galactose?
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- Treatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.Which aldoses are oxidized to optically inactive aldaric acids: (a) D-erythrose; (b) D-lyxose; (c) D-galactose?What aldoses are formed when the following aldoses are subjected to the Kiliani–Fischer synthesis: (a) d-threose; (b) dribose; (c) D-galactose?
- Treatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?
- An oligosaccharide isolated from an organism is found tocontain two glucose residues and one galactose residue.Exhaustive methylation followed by hydrolysis producedtwo glucoses with methoxy groups at positions 2, 3,and 6 and galactose with methoxy groups at positions2, 3, 4, and 6. What is the structure of the originaloligosaccharide?An optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.Given the following structure of aldose, (a) how many chiral carbons are there? (b) is it a reducing sugar? and (c) is it an L or D sugar?