SP08E3KEY-1-1 - Sp08_215_E3_KEY Draw the Haworth projection...

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Sp08_215_E3_KEY A. ( Org. Lett. 2008 , 10 , 1775) O O O NO 2 OH CH 3 NaBH 4 CH 3 OH O O NO 2 OH CH 3 OH HCl + CH 3 OH Draw the Haworth projection of the major product that is a furanoside. Note that the furanoside contains an acetal (as no water is added.) OCH 3 H H H OH CH 3 H O NO 2 I (23 points ) 3 4 B. ( JOC , 2008 , 73 , 3460) O OH H N C OH O OCH 3 O OH HO HO 1 equivalent NH 2 CH 3 O OH H N C OH O N H O OH HO HO CH 3 C. ( Tet. Lett. , 2008 , 49 , 3112) H OH HO H CH 2 OH H OH O 1) CH 3 NO 2 , NaOCH 3 , CH 3 OH 2) H 3 O + Draw the Fischer projections of the two products. H OH HO H CH 2 OH H OH OH CH 2 NO 2 H OH HO H CH 2 OH H OH H CH 2 NO 2 HO H 3 4 3 D. ( JOC , 2008 , 73 , ASAP, MacMillan) O HO HO OH OCH 3 O O O OH OCH 3 The products are: ( Circle all that apply ) enantiomers diastereomers epimers meso anomers O + H 2 O TsOH or H 2 SO 4 CrO 3 . py O O O O OCH 3 3 3 accept either stereoisomer at the hemiacetal + CH 3 OH
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Sp08_215_E3_KEY A. ( Tet. Lett. , 2008 , 49 , 3112) II ( 22 points ) H OCH 3 H H H OH OH O HO OH i) This furanoside is: ( Circle one answer in each box ) iii) Catlyatic acid is added and the furanoside is in equilibrium with the pyranoside. Draw a Haworth projection of the ! -pyranoside formed.
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