Winter 2006 KEY-3 - Name: KEY Page (W.06.215.E4.p1) I....

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Name: KEY Page (W.06.215.E4.p1) N S S H 2 O, H 3 O A . J. Org. Chem. 2006 , 71, 2547. O O O O OH excess NaH OH O O CH 3 HO C C O O CH 3 O C C H MgBr H 1. excess H 3 O, H 2 O 2. excess Swern oxidation (DMSO, C 2 O 2 Cl 2 , Et 3 N:) O CH 3 HO C C H H O + 5 5 H 2 O, H 3 O 5 5 D. Org. Lett. 2006 , 8 , 903. 5 5 excess CH 3 I + O O O O OCH 3 OCH 3 O HO HO OH OCH 3 OCH 3 5 Complete the following transformations as indicated by the data provided. You may use the abbreviation LDA (lithium diisopropyl amine). Provide stereochemistry where appropriate and number sequential steps accordingly. B. J. Org. Chem. 2006 , ASAP. O H N O HS HS C. O O 1. LDA 2. O H 3. H 3 O, H 2 O, heat OR OH , H 2 O, heat + H 2 O + HO 5 5 5 I. OR alpha OR beta acceptable O H OCH 3 H H OCH 3 H OH H OH CH 2 OH hemiketal ok hemiacetal ok many other answers acceptable too
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Name: KEY Page (W.06.215.E4.p2) A. 5-Fluorouracil is a commonly used pyrimidine antagonist. It functions to inhibit DNA synthesis both by blocking the formation of normal pyrimidine nucleotides via enzyme inhibition and by interfering with DNA synthesis after incorporation into a growing DNA molecule and is used in chemotherapy. Assuming acidic conditions , draw a mechanism showing the substitution of 5-fluorouracil for the diphosphate group of A to form B . You may use H-B or B: as a general acid or base, respectively. O O OH O P HO O OH P O P OH O O OH OH N H NH O O F O O OH P HO O OH N NH O O F + HO P O P OH O O OH OH A B H B O O OH O P HO O OH P O P OH O O OH OH H O O OH P HO O OH N H NH O O F O O OH P HO O OH N NH O O F H B: 28 O HO HO HO O CH 2 OH excess NaBH 4 CH 2 OH OH H OH H OH H H HO C O 2) Draw the cyclic hemiacetal alpha-D-pyranose chair AND the Haworth structure of the furanose form for
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Winter 2006 KEY-3 - Name: KEY Page (W.06.215.E4.p1) I....

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