In pharmaceutical research, structural analogs (or derivatives) of drugs are often made...

In pharmaceutical research, structural analogs (or derivatives) of drugs are often made in order to see if they have similar biological properties. Below is a structural analog of Peramivir (Problem 11.46) called A.

(a) Complete the drawings of the alternative chair conformations of A, making sure to note the numbering of the ring atoms. Which of the alternative chair conformations is more stable? (Chapter 2)

(b) A is formed from the cyclization of B. Which two functional groups in B react to form A? What is the name of the new functional group formed when these two groups react to close the ring? (Hint: We studied this reaction in Chapter 9.)

Problem 11.46

Consider the experimental antiviral drug Peramivir, shown below, a neuraminidase inhibitor recently supported by the U.S. Department of Health and Human Services as a treatment for Influenza A (H1N1), “Swine Flu.”

(a) What is the molecular formula of Peramivir? (Chapter 1)

(b) Identify the functional groups labeled with arrows in the structure above. If any alcohols or amines are present, determine if they are primary, secondary, or tertiary. (Chapter 1)

(c) How many total stereocenters (if any) are present in Peramivir? (Chapter 6)

(d) Determine the maximum number of possible stereoisomers for this molecule. (Chapter 6)

(e) Fill in the blanks: There is/are ____________ enantiomer(s) and ____________ diastereomer(s) of Peramivir. (Chapter 6)

(f) One of the stereocenters in Peramivir is known to have the R-configuration. Label this stereocenter in the structure. (Chapter 6)

(g) Compare each molecule below with Peramivir and identify it as “identical,” “enantiomer,” “diastereomer,” or “none of these.” (Chapter 6)