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PS_13_Key - Tali «Kw-v 1I Problem Set#I 2 I Suggested...

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Unformatted text preview: Tali, «Kw-v; 1I Problem Set #I 2 I. Suggested Carey 7th Edition questions: Chapter 25: 25.24, 25.25, 25.28, 25.33, 25.34, 25.37, 25.38 : 2. Write 21 Fischer projection of the open-chain form of each of the following: OH b gimme, {Ni-w” '5} -. MIN; BMW. 3. Convert the following Fischer projections to OL-furanosides: CH0 CH0 , . {:1 i 4. Convert the following Fischer projections to B-pyranosides; CH0 {2% H CHO 0” H OH [ : ‘ H OH L/e ‘ H OH , _ ,I ,1 HO H 'D/X , ~ or: 1? H OH M n at H OH Hat, may “ Wflfiflwfi/ H OH H OH am CHZOH CH20H b—~ M1033, 13—1?va CHO E HO H H OH 0 j H OH "“ g H OH ; CHZOH ' M 1 T) ‘ tflMfiz 11 CHO H OH Ho H Ho H H OH CH20H CHO H OH Ho H H OH CHZOH CHO Ho H H OH H OH CHQOH CHO Ho H Ho H H OH CHEOH (3‘) Mix) (ill ammo £31.!st 5. Provide the reagents to accomplish the following transformations. More than, one step might be required for each transformation. CHEOH H OH Ho H Ho H H OH CH20H COZH H OH HO H H OH CHZOH CHZOH CHZOH H OH HO H Ho H + H0 H H OH H OH H OH H OH CHZOH CHZOH CH0 CH0 H OH Ho H Ho H + H0 H HO H Ho H H OH H OH CHZOH CHZOH Predict the product for the following transformations. stereochemistry of the product. HoOH OH ’0 HOSE::LQ§/H OH Me 30+ EtO OEt EtOH, cat. H+ O O )LJL Ph 0 Ph pyridine MeOOH OMe % OMe Me —, cat H+ NalO4, H2804 ————-—-——-——> When necessary please explicitly show the 6. Provide a reasonable mechanism to account for the following transformations. When necessary please explain the observed stereochemistry. CH0 0 o H3O+ H OH O H —> H OH OH H OH OH H OH D—Altrosan CH2OH ‘ CHO ‘- y H Z0H awe/LITA o ”‘ OH HO 3H 165°C Mime HO H H HO' 3 H ‘ H S0H H 1 OH (DCH20H D-Galactose 5 Wauimk E E WEAR, aqua-2E MEMMM LT ‘ E §: 4: /9 l “K 4‘3 Please provide a mechanism to explain the following experimental observation: HO H3O+ H0 [40% ——> HO 0 + open forms HO OMe krel = 2000 HO OH 2—deoxy-D-glucose HO H30+ HO HO O ———> HO O + open forms HO OMe krel = HO OH OH OH D—glucose ‘ 549% bh QM ¢_ Maud/3%.», 5514311., m... (.3 ‘10 l) v ‘ V . “9% (\79 Jig-$33 @fi «3 QMQFQMQ figmré, Ex: 02» CM E:va Please provide a mechanism to explain the following experimental observation: HOHZC CHZOH HOH20 CHzOH O O H O+ - H H HO OM —-—-—>3 H HO +open forms 8 krel : 105 H OH 5 . OH H OH H i methyl-a-D-fructofuranoside CH OH l 2 CHQOH ‘ HO H H O + H0 H H H HO H30 0 H HO +open forms . H OMe _ ‘ krel — 1 H OH E OH H l OH H ; methyl-a-D—glucofuranoside V l ' ‘“ 5 WC- liege/m. ‘ mm 3 “a” ma lag. {flit-Em 2‘? m}; filial}; 0 @DK om _ .4 ”94%“ isa gall ; H all :1 .54.} in l r‘ 9 i; M x N ? W Wakwm WM 0% 2/9 CWbMfiw H l5. 2)) lob CHO ‘ H OH NH2 + % HO H + H20, H3O & H OH heat H OH é CHZOH Me 1' V???" “S ‘ Rafi-“H. 1 ’DM ~v.«mmm_r V ‘A‘ 3 Z ..m...'.'w~m-.w~?,~ CHO H OH HO H H OH H OH CHZOH D—glucose HO 1 HO NH2 3 trace H" H OH ; A {T IO ...
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