Chapter 23: Q21P (page 1225)
Draw the structures of the compounds named in Problem 23-20 parts (a), (c), and (d). Allose is the C3 epimer of glucose and ribose is the C2 epimer of arabinose.
Chapter 23: Q21P (page 1225)
Draw the structures of the compounds named in Problem 23-20 parts (a), (c), and (d). Allose is the C3 epimer of glucose and ribose is the C2 epimer of arabinose.
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Get started for freeCellulose is converted to cellulose acetateby treatment with acetic anhydride and pyridine. Cellulose acetate is soluble in common organic solvents, and it is easily dissolved and spun into fibers. Show the structure of cellulose acetate.
Treatment of either anomer of fructose with excess ethanol in the presence of a trace of HCI gives a mixture of the α and β anomers of ethyl-D-fructofuranoside. Draw the starting materials, reagents, and products for this reaction. Circle the aglycone in each product.
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the hydrolysate is found to be tagatose. The following information is known about tagatose:
(1) Molecular formula C6H12O6
(2) Undergoes mutarotation.
(3) Does not react with bromine water.
(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.
(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives 1,3,4,5-tetra-O-methyltagatose.
(a) Draw a Fischer projection structure for the open-chain form of tagatose.
(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose.
An important protecting group developed specifically for polyhydroxy compounds like nucleosides is the tetraisopropyl-disiloxanyl group, abbreviated TIPDS, that can protect two alcohol groups in a molecule.
(a) The TIPDS group is somewhat hindered around the Siatoms by the isopropyl groups. Which OHis more likely to react first with TIPDS chloride? Show the product with the TIPDS group on one oxygen.
(b) Once the TIPDS group is attached at the first oxygen, it reaches around to the next closest oxygen. Show the final product with two oxygens protected.
(c) The unprotected hydroxy group can now undergo reactions without affecting the protected oxygens. Show the product after the protected nucleoside from (b) is treated with tosyl chloride and pyridine, followed by NaBr, ending with deprotection with Bu4NF.
All of the rings of the four heterocyclic bases are aromatic. This is more apparent when the polar resonance forms of the amide groups are drawn, as is done for thymine at left. Redraw the hydrogen-bonded guanine-cytosine and adenine-thymine pairs shown in figure 23-24, using the polar resonance forms of the amides. Show how these forms help to explain why the hydrogen bonds involved in these pairings are particularly strong. Remember that a hydrogen bond arises between an electron-deficient hydrogen atom and electron-rich pair of nonbonding electrons.
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