Compound A below is a key intermediate in the synthesis of keto-myo-inositol B. Suggest a synthetic route for the preparation of A from D-glucose C giving structures for all of the intermediates in your scheme. Ph3CO. HO., НО HO HO HO, НО "ОН ОН OH CH3 CH3 Ph А В C
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- Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.Atorvastatin (Lipitor) is used to decrease patient serum cholesterol levels. It works by inhibiting an enzyme called HMG-COA reductase. See"Connections to Biological Chemistry" one synthesis of atorvastatin that produces the desired single enantiomer of the final product, the following reagents are used. Draw the structures of synthetic intermedi- ates A and B. In -Cl NaCN НО. A B DMSO PyridineWhich one of the following statements best describes the chemistry of ring A? E B OH он, A H Oleandrin is a toxic cardiac glycoside found in the poisonous plant, oleander (Nerium oleander L). It has a very long IUPAC name: acetic acid [(35,5R, 10S,13R,14S, 16S, 17'R)-14-hydroxy-3-[[(2R,4S,5S,65)-5-hydroxy-4-methoxy-6-methyl- 2-tetrahydropyranyl]oxy]-10,13-dimethyl-17-(5-oxo-2H-furan-3-y)-1,2,3,4,5,6,7,8,9,11,12,15,16,17- tetradecahydrocyclopenta[a]phenanthren-16-yl] ester Ring-A can act as a reducing sugar Ring-A can undergo mutarotation Ring-A is non-reducing O Ring-A is a furanose
- Write the structure of the compound E,E-2,4-Hexadien-1-ol and label each non-equivalent carbon with a letter, A,B,C..Give the structures of the cycloadducts formed -SO₂Ph + PhH t. amb. ➤ A + Ph CO₂Me + с CO₂Me Ph Ba Give the chemical structure of (2R.3S)-2,3-dibromopentane b. Identify the following pairs of compounds as either enantiomers, diastercomers, or identical CN .COOH он CCH но CCH and NC COOH Give the structure of any reagent that can be used to enantiomerically resolve R- and S- ibuprofen
- A chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?24). What is the major organic product of the following reactions? -CH₂-CN Å (A) 1. LDA/THF CH₂-COOH (B) COOH OH (C) 3. H₂O+, Heat H₂ ? LOH (D) (E) CH₂-CN OH2. Compound A, C;H100 , is one of the basic building blocks of nature. All steroids and many other naturally occuring compounds are built from compound A. Spectroscopic analysis of A yields the following information: IR: 3400 cm-'; 1640 cım- IH NMR: 1.63 & (3 H, singlet); 1.70 ô (3 H, singlet); 3.83 6 (1 H, broad singlet); 4.15 8 (2 H, doublet, j = 7 Hz); 5.70 ô (1 H, triplet, ) = 7 Hz) (a) How many double bonds and/or rings does A have? (b) From the IR spectrum, what is the identity of the oxygen-containing functional group? (c) What kinds of protons are responsible for the NMR absorptions listed ? (d) Propose a structure for A.
- 11. Compound A, C9H17N, is an optically inactive alkaloid, containing a tertiary amine that is not located at the bridgehead of the structures fused bicyclic ring system. Exhaustive alkylation of A with methyl iodide, followed by a Hofmann elimination reaction resulted in a racemic mixture of chiral tertiary amine products B, C10H19N. Provide a structure for A and one of the enantiomeric products B.A chiral amine A having the R conguration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?[ 16 ] which of following compound(s) is/are neither acetal nor hemiacetal ? он Но Он осH-CHз CHз ОН OCH3 (1) ( II ) ( III ) (IV ) (V) (a ) compounds III and V (b) compounds Il and II (c) compounds I and V (d ) compounds IV and V (e) compounds I and IV