Simvastatin (trade name: ZocorTM) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. H H HO,, H H H O H H H H O H O HE H
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- Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?Simvastatin (trade name: Zocor™M) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. HOL. O CH3 H O H Ou yot H O XII H по / CH3Diltiazem is prescribed to treat hypertension, and simvastatin is a cholesterol-lowering drug. Locate the chirality centers in each.
- Ans: 2. Assign the absolute configuration of the chirality center as R or S. O HO- Ans: Assign the absolute configuration of the chirality center as R or S. Ans: OH 3. Drawn below is the structure of Crestor® (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S. | NH 4. What is the relationship of the following two structures? OH OHI NH OH OH A. Enantiomers B. Diastereomers. C. Constitutional isomers D. Identical Ans: NH CO₂H 5. What is the relationship of the following two structures? OH OH A. Enantiomers B. Diastereomers C. Constitutional isomers D. Identical Ans: Loo HO OH 6. What is the relationship of the following two structures? HO HO \,.. ...NH محمد HO OH eilte neu-1071 Mamos a diartwollen preto aCoibacin B is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites. Assign the configuration of each chiral center in coibacin B H.8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomers
- Aldosterone, a steroid involved in regulating blood pressure, is shown without dash-wedge notation. How many chiral centers does aldosterone have? OH HO, Aldosterone(a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?Identify the absolute configuration of the chirality centers in each of the following compounds as R or S. Note: if multiple chirality centers are present, indicate the stereochemical designations as: RR, SS, RS, or SR. (Other terms used for chirality center include chiral center, stereocenter, and stereogenic center.) H Br !!!! H₂N CO₂H но H CH3 H CH3 OH OH H Ωσ HI!!! HO HO Br CO₂H H
- 8. Which of the following descriptions provided is an accurate description of the given molecule below CH2CH3 H. CH3 CH2 H: °CH3 CH2CH3 А. Has two chirality centers and a plane of symmetry, therefore it is achiral В. Has two chirality center, therefore it is chiral С. Has two chirality centers and a plane of symmetry, therefore it is chiral. D. Has two chirality centers and no plane of symmetry, therefore it is achiralDiastereomers are a type of a stereoisomer. Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. OH OH НО Но ÕH ОН How many chiral centers are present in one of the structures above? 1 O 2 O0 Are the structures mirror images of each other (i.e., are ALL of the chiral centers exactly opposite)? no yes I can not tell. How are these two structures related to each other? Diastereomers Non-isomeric (different molecular formulas) O Constitutional (same MF but different connections) Enantiomers (non-superimposable mirror images)5. Consider the following pairs of structures. Identify the relationship between them (enantiomers, diastereomers, or identical compounds. HOH2C H OH H OH HO H Br H3C Н H H₂CH₂C CI Br H CHO CH3 I CH3 OH OHC Н H OH H OH Bell!! H3C, HO H Н.С H CH₂CH3 CH3 CI HỌ,H CH₂OH Br