Chapter 5: Q.53 (page 208)
Label the stereogenic centers in paclitaxel, the chapter-opening anticancer drug, as R or S.
Short Answer
The stereogenic centers of paclitaxel are labeled as follows:
Chapter 5: Q.53 (page 208)
Label the stereogenic centers in paclitaxel, the chapter-opening anticancer drug, as R or S.
The stereogenic centers of paclitaxel are labeled as follows:
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Get started for freeDetermine if each compound is identical to or an enantiomer of A.
a.
b.
c.
A sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S-adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.
a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.
b. Label each stereogenic centre as R or S.
Indicate a plane of symmetry for each molecule that contains one. A molecule may require rotation around a carbon-carbon bond to see the plane of symmetry.
a.
b.
c.
d.
a. Locate all the tetrahedral stereogenic centers in discodermolide, a tumor inhibitor isolated from the Caribbean marine sponge Discodermiadissoluta.
b. Certain carbon–carbon double bonds can also be stereogenic centers. With reference to the definition in Section 5.3, explain how this can occur, and then locate the three additional stereogenic centers in discodermolide.
c. Considering all stereogenic centers, what is the maximum number of stereoisomers possible for discodermolide?
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