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problem set 6

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University of British Columbia
CHEM 313

Chem 313 Problem Set #6 2010 1. The synthesis of polynucleotides has been studied and refined for years. Some of the original work in this field was carried out at UBC, by H.G. Khorana. His lab’s methods of forming the phosphodiester backbone of polynucleotides involved the use of dicyclohexylcarbodiimide (DCC) with 5’ phosphorylated precursors. A potential byproduct of this reaction is the formation of 5’-3’ cyclic phosphates. What is the mechanism of this reaction? O T T O HO P O O O O DCC OH P HO O OH 5'-TMP 2. The rate of acidic hydrolysis of trityl ethers is very dependent on the substituents on the phenyl rings. Predict (using >,< or =) the relative rate of each of the following reactions. Provide structural evidence supporting your claim. RO TFA HO General reaction: O O OCH3 OCH3 a) O O O O O O OCH3 b) NO NO 2 2 O O O O O O NO 2 3. Show the reagents you would use for the following transformations. A HO HO A A O HO O O O O P O O O A P P O O O O A A O O HO O
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