Following is a structural formula of desosamine, a sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago.
(a) Name all the functional groups in desosamine. (Chapter 1)
(b) How many chiral centers are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it? (Chapter 6)
(c) Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial. (Chapter 2)
(d) Which of the alternative chair conformations for desosamine is more stable? (Chapter 2)
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