CHEM215W06_key[1] - Name Page1(W.06.215.E3.p1 I(23 points Three transformations are shown below In each case a Chem 215 student suggested a set of

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Name:___________________ Page1 (W.06.215.E3.p1) O BnO OCH 3 OBn O Bn = CH 2 Ph O BnO OCH 3 OBn HO H 3 O + , H 2 O Three transformations are shown below. In each case, a Chem 215 student suggested a set of reaction conditions for carrying out these reactions. If you think the product that would form under these conditions is the one that is shown, please write "yes" in the answer space. If not, please draw the single major product that would be expected instead of the one shown. In cases where enantionmers, diastereomers, or anomers from, you only need to draw one of them. + H 3 N C CH 2 OH O OH + H 3 N C CH 2 OH O OCH 3 1 eq NaH 1 eq CH 3 I H O H H H H H OAc H OH OAc HO A c H H H H OH H CH 2 OAc 1) 2) H 3 O + (protonate) H (H 3 CH 2 C) 3 SiO N N N N NH 2 O OSi(CH 2 CH 3 ) 3 H H B. Complete the following transformation s. (JOC 2006 , 71 , 1009) (H 3 CH 2 C) 3 SiO N N N N HN O OSi(CH 2 CH 3 ) 3 H H O CH 3 CH 3 CH 3 I. (23 points) H O H H H H H OAc H OH OAc also accept alpha form Cl O N or TEA OR anydride, or thioester, or ester 4 5 5 5 O BnO OBn HO OH H also accept alpha form + H 3 N C CH 2 OCH 3 O OH + H 3 NC C CH O - O CH 3 H 3 C CH 3 OH HCl 4 H + H 3 C CH OCH 3 O CH 3 H 3 C H (i) (ii) (iii) Li (i) (ii) O Ph OH HO H H H 1 eq
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Name:___________________ Page2 (W.06.215.E3.p2) The primary alcohol of α -D-allopyranose reacts with acylating agent 1 . This acylation is described in the literature ( Biosci. Biotechnol. Biochem. 2005 , 69 , 833) as irreversible, "the enol freed by
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This note was uploaded on 05/08/2009 for the course CHEM 215 taught by Professor Gottfried during the Fall '08 term at University of Michigan-Dearborn.

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CHEM215W06_key[1] - Name Page1(W.06.215.E3.p1 I(23 points Three transformations are shown below In each case a Chem 215 student suggested a set of

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