Winter 2006 blank-2 - Name Page{Wfl321 5.E4.p1 I Complete...

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Unformatted text preview: Name: Page {Wfl321 5.E4.p1} I. Complete the following transfonnatipns as indicated by the data provided. You mayr use the abhreviatim LDA {lithium diisopropyl amine}. Provide steneoohen'istnir where appropriate and number sequential steps aocordinfly. A J. org. Chem. 2005, n 254?. H201 H3§J fl - + E exsess NaH 0%‘0—Q excess CH3I HOCHg—Q DC B. J. Org. Chem. 20%. ASAP. lHZCI. Hat-IQ E+|1+l E C “a. +H20 CI fl H—milk—“I23-|'u'lgBrE7< D. Org. Lett. HIDE. 8. 903. 9 HQ: CH3 1. excess H30, H20 2. excess Swern oxidation IDMSD.C202CI21 Eta a H Csc-H Name: Page iW.EtB.215.E4.p2] II. A. 5-Fiuorourecil is a commonly used pyrimidine antagonist. It functions to inhibit DNA synthesis both by biockhg the formation of non'nol pyrimidhe nucleotides yie enzyme hhihition end by interfean with DNA synthesis after incorporation into a vowing DNA molecule and is used in chemotherapy. Assuning acidic conditions, draw a g mechanism showing the substitution of fi-fluorouraoi for the diphosphate group of A to form 3. You may use HvB I . ..— I—— l.- HILL-I B. Complete the folowing honsforrnetions as indicated by the data provided. Proyide stereochemish'y where appropriate 1] CHEDH Ht) 0 excess Na 3H4 —h~ ”0 Ho o H20 2] Draw the cycle hemiecetol alpha-D-pyrenose ct'iair AND the Haworth structure of the furenose form for the open chain Fisher projection show below. it c-H H HE]I H DH H H OH OH CHZOH D 3i 1} 2 eq. LDA HE] —P— D 2} 1 eq. cchHchger 3} Haori) H20 E Name: Page {W.Dfi.215.E-t.p3} III. A. Peptide-derived compounds are attreotiue research targets Compound C. was reoently synthesized (J. Org. Chem. T1, 21535}. However, it was found that eompomd it easily rearranges to oompound D in a haste alien. 'tI'tuiite a mechanism to aooount for this transformation. Reminder, we're in best: solution. Use HE! and B for a general add and base, respectively. E. It toms out that the final produot {compound E} has specific slereodtenistry We didn't want you to worry about stereoohen‘iistxy when drawing the mechanism} and is optically aotiye {rotates oiwlady polsn'zed light}. However. if this oompoond is ptaoed in a haste solution over a oertain period of time. the oompound no longer rotates eirmtany polarized light. Assuming that the eongooond hes not degraded and has retained its mess and oonneofltrihr. use piohll‘eetillmtmdons AND words to explain why the solution is no longer optiadly active. Compound D Name: KEY Page {W.Dfi.215.E-t.p4} Iv. Mamepeptlmycin-E is a natural glvodpeptide derivative and has been recently been synthesized {Org Lett. 2W3. El, 1505}. A derivative of mannopeplimvinvE is shown below. Cicle vfltether each of the slereooenlers is R or 3 {three boxes below-tr]r and circle the appropriate number of fisncfionaliliee in the large box below. 13 i—circleone 13 "'—circleone 13 circleone' '1— 13 "I‘— 13 circleone "I‘— 13 I ts *omemn 13 "I—UI'CIE one ltetal fl 1 2 QHHHHHHHQH emf {112 4553'391‘3111213 o'rcleonez Guest You left your brain at home and accidentally reconelt'rme this molecule in very. very strong aqueous acid. and heat it up overnight. From the list of poterttial side—products shown below. cimle whim products that would likely be any of the products of the total product mixture. Points wlll be deducted for Incorrect answers. 0 SH 0“ H0 0H H0 ten/(“i HD\%OH oH a H3" E“ oH “0 o o H3N U. CH3 Name: Page {w.ss.21 5.91.sz 'U'. Cmpieie ii'ia following transformations as indicated by he data provided Provide stemmemistry v-i'iere sppmpfleie. You may use the abbreuieiien LDA {Iflhium diiseprupyl amine}. A. J. Dry. Chem. 2M6. F1, 254?. excess CHaCi (K5 [Eb—C H3 H2504 H20 Hag/1&5” —@—- Hzflrflfi 2. H30 H20 [workup] B. J. Chem Ed. 2006. 63. 2T3. 1) 1eq.LDA + CH 0H 3 Hack/OJLocHa _®_,_ 2} H30.H2CI (121$... ”is“ [CHsC H213” Cstszosfi-‘s E D. Nucleic Adds Symp. Ser. 1935. 16. 1T3. 0 0 aqueous excess NH3 e (“N | NH 0 heat H=C\/\e'§=0 N NANJLCHg H NH fl solid support Draw the esmpistsiy mobile compound with the highast molecular waighl‘. _ Name: KE‘r Page [W.DE.215.E4.pB] VI. A] The compound Aspartame has the stmcture shown below and is derived from L-phenylalanlne and L-aspartlc acid. Draw the absolute stereochemistly of Aspaltame at all the stereooenters h the box. The pl tor aspartame Cl would most likely be Wilma 0 a] betweer‘t pH 1 and .1 i p} bemoan pH 4 and T “2“ o OCHS c] bemoan pH r and 1c E B} Fill in the boxes in order in the synthesis of Aspartame. The synthesis of the dtpepltde Aspartame becomes more chalengtng than a typical dipsptlds synthesis due to the side chain carbon-:ylic acid group on the asparttc acid. Staring with Aspfiiule provide a synthesis of Aspartame as directed below. You may use abbreviations for the reagents used to protect the amino acid, but must draw their stmctures in the product boxes. 0 0 HEN e'CH3 H0 HEN D‘cHg Cl mmew) Aspfliute 5}” I DGHa CFacmHtTFA} + C02 El C]: Draw a mechanism for the bimolecular aldot reaction. You may use HE and E as a general acid and base. ...
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