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Organic Chemistry 2 Final - Part 3 of 6
SAMPLE
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28. Carbohydrates / Glycoside / Problem 9
Problem 9

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.
Chemical structure of a glycoside protecting group on β-D-mannose.
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.

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