2. Provide the Haworth projection for α-(D)-idopyranosyl-(1,1)-ẞ-(D)-glucofuranose (the Fischer projection for idose is provided below). HO -H H- -OH HO -H H -OH CH₂OH (D)-idose
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- 1. In the space provided, draw a Haworth projection for the alpha anomer of the following monosaccharide Fischer projection. H но CHO OH -H H- OH H- FOH CH₂OH1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.Draw the Haworth projection for B-D-xylose The Products of the reaction of L-glucose with the following L-glucose [1] NH2NH4 [2] Ac2O,NaOAc [3] N2OCH3 Products of the reaction of D-threose with the following D-threose [1]NACN, HCI [2] H2, Pd-Baso, [3] H3O*
- 2) a-Draw the proper flat, Haworth form and most stable chair conformation for the B- anomer of L- glucopyranose b- Write the systematic name of this compound O: HO- НО—н НО H FOH HO-H -O- L-Gulosem) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за поч4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОН
- Draw the Haworth or Chair Haworth structures of the following disaccharides: (a) α-D-glucopyranosyl-(1,4)-β, D-galactopyranose (b) β,D-galactopyranosyl-(1,4)-α-D-glucopyranose (c) β-D-glucopyranosyl-(1,4)-α,D-galactopyranose. Identify all anomeric carbons and hemiacetal, acetal, hemiketal, and ketal linkages.НО Но н Н- НО он Н Н HO H OH оно н Н H. H Н ОН Н H н 아처 OH CH НО.What is the Fischer projection of the monosaccharide from which the following glycoside was prepared? НО. H- H Н CH.OH :0 -OH OH -OH CH₂OH HO- НО H ОН CH₂OH " H -H OH CH₂OH OH НО OH Н- Н- CH₂OH O H OH ОН CH₂OH Ш H— НО НО CH₂OH O OH H -H CH₂OH IV
- N-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Ne7. Draw the Haworth structure for the following monosaccharides a. H НО H c=0 H + но - н 3 4 Н 5 - ОН - OH 애 CH₂OH 6 D-Mannose b. H 0 = с H - C - OH HO-C - H H - C - OH H - C - ОН CH₂OH GlucoseDraw the Haworth projection of both pyranose and both furanose forms of D- Idose with all stereocenters accurately portrayed. You do not have to label the name of the form you drew H-CO HO -H H -OH HO -H OH OH HOH2C H- OH CHO OH OH CH2OH D-Idose line drawing D-Idose Fischer projection