Problems-140C-2006winter-Final

Problems-140C-2006winter-Final - Problem 1 Starting from...

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1 Problem 1 Starting from Boc-Lys-O t Bu, provide a strategy for the synthesis of Glutamic acid. Show the chemical structures of all intermediates and provide all the reagents needed for all steps to perform the synthesis. H 2 N O OH O OH Boc-Lys-O t Bu ? Problem 2 Phenylglycine is a non natural amino acid. Using Strecker synthesis and appropriate reagents and techniques, provide a synthetic approach for the synthesis of L-phenylglycine starting from nitrobenzene. H 2 N OH O ???? NO 2 Problem 3 (25 points) Starting from polystyrene methyl chloride resin: Using the appropriate protected amino acids, reagents and techniques, provide a synthetic approach for the solid-phase synthesis of the following product: H N N H H N OH O NH O O HO O OH O O Problem 4 Draw the chemical structure of the major products expected from each of the following reactions. A) Pro-Lys-Val N C S A HF B + C Excess B) N H Boc OH O H 2 N O O tBu + DCC in DCM D + E + F PS Cl
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2 Problem 5 Give the major product of each of the following reactions. a) O HNO 3 b) N N CH 3 I c) N Cl C 6 H 5 Li d) N H Br 1) Mg/Et 2 O 2) CO 2 3) H 3 O + e) 1) (Ph) 3 P f) 1) O3 2) CH 3 -S-CH 3 g) Cl O 1) AlCl
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This note was uploaded on 04/14/2009 for the course CHEM140C 234234 taught by Professor Nefzi during the Spring '09 term at UCSD.

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Problems-140C-2006winter-Final - Problem 1 Starting from...

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