Glycoside Practice Problems

What is the name of the following compound?

What is the name of the following compound?

Show the products when Salicin undergoes acid-catalyzed hydrolysis.

Some protecting groups can protect two hydroxy groups on a carbohydrate at the same time. One such group protects the OH groups at carbon 4 and carbon 6 of β-D-mannose, as shown below. 

a. To what functional group does this protecting group belong? 

b. What reagent is employed in the synthesis of such protected compounds? 

c. When this blocking group is coupled with β-D-mannose, a new chiral center is formed. What is its location? 

d. Draw the compound's other stereoisomer and assess which stereoisomer should be more stable.

Tetraisopropyldisiloxanyl, or TIPDS, is an important protective group that was created specifically for polyhydroxy substances like sugar. TIPDS can shield two alcohol groups of a molecule.

a. The isopropyl groups around the Si atoms hinder the TIPDS group slightly. Which OH of 1-methoxy-α-D-arabinofuranose has a higher chance of reacting with TIPDS chloride first? Draw the product with one oxygen attached to the TIPDS group.

b. The next oxygen nearest to it is reached once the TIPDS group has been connected to the first oxygen. Draw the final product with TIPDS attached to two oxygens.

c. Now that the oxygens are shielded, the unprotected hydroxy group can undergo reactions. Draw the final product result of treating the protected 1-methoxy-α-D-arabinofuranose from (b) with tosyl chloride, pyridine, and then NaBr.

The hydrochloric acid-catalyzed reaction of either α-D-ribose or β-D-ribose with excess methanol produces a mixture of α and β anomers of methyl D-ribofuranoside. Illustrate the reactants, reagents, and products for the reaction. Identify the aglycone in the products by circling it.

What products will be formed when D-mannose reacts with ethanol and HCl?

Draw the product(s) obtained in the reaction of D-altrose with ethanol and HCl.

What product(s) will be obtained when β-D-gulose reacts with ethanol and HCl?

Provide the structure of the following glycoside.

propyl α-D-altropyranoside