ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Question
Chapter 27, Problem 28P
Interpretation Introduction
Interpretation:
A mechanism for the reaction of the glycosyl donor with the glycosyl acceptor in solid-phase synthesis of oligosaccharides is to be written. The regioselectivity of the given reaction is to be explained.
Concept Introduction:
The epoxidation of
The regioselectivity of
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4. An iterative approach to oligosaccharide synthesis involves the use of protected glycals (sugars with
C1-C2 double bond) as shown below. The product from the reaction of the first glycal with DMDO under
anhydrous conditions is treated with another suitably-protected glycal to form a disaccharide glycal, and
the process can be repeated to form a trisaccharide glycal, and so on... Crucial to the success of this
approach is the stereoselective formation of the intermediate A in the scheme below. Draw the
structure of A.
DMDO
CH₂Cl2
A
OH
ZnCl₂, THF
OH
Deduce the structure of the disaccharide isomaltose from the following data.a. Hydrolysis yields D-glucose exclusively. b. Isomaltose is cleaved with α-glycosidase enzymes. c. Isomaltose is a reducing sugar. d. Methylation with excess CH3I, Ag2O and then hydrolysis with H3O+ forms two products:
The disaccharide lactulose consists of a D-galactopyranose subunit and a D-fructofuranose subunit joined by a B-1,4'-glycosidic linkage. After treatment
of lactulose with 1. excess CH3I/Ag20, 2. HCI/H20, the D-galactopyranose subunit was found to have one nonmethylated OH group, whereas the
D-fructofuranose subunit had two. Draw the structure of a-lactulose.
Chapter 27 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 27.1 - Problem 27.1 Write a structural formula for the...Ch. 27.1 - Prob. 2PCh. 27.1 - Prob. 3PCh. 27.2 - Prob. 4PCh. 27.3 - Prob. 5PCh. 27.3 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.5 - Prob. 8PCh. 27.5 - Prob. 9PCh. 27.6 - Prob. 10P
Ch. 27.7 - Prob. 11PCh. 27.9 - Prob. 12PCh. 27.12 - 27.13 Modify Figure 27.12 so that it corresponds...Ch. 27.13 - Prob. 14PCh. 27 - Prob. 15PCh. 27 - Prob. 16PCh. 27 - Prob. 17PCh. 27 - Nebularine is a toxic nucleoside isolated from a...Ch. 27 - Prob. 19PCh. 27 - The 5-nucleotide of inosine, inosinic acid...Ch. 27 - Prob. 21PCh. 27 - (a) The two most acidic hydrogens of uracil have...Ch. 27 - The phosphorylation of -D-glucopyranose by ATP...Ch. 27 - When 6-chloropurine is heated with aqueous sodium...Ch. 27 - Prob. 25PCh. 27 - Prob. 26PCh. 27 - Prob. 27PCh. 27 - Prob. 28PCh. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...Ch. 27 - Oligonucleotide Synthesis In Section 27.6 we noted...
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- In glycoside formation, the hemiacetal functional group of a cyclic monosaccharide is converted to an acetal group by reaction with a(an)arrow_forwardA D-aldohexose A is formed from an aldopentose B by the Kiliani-Fischer synthesis. Reduction of A with NABH4 forms an optically inactive alditol. Oxidation of B forms an optically active aldaric acid. What are the structures of A and B?arrow_forwardarrow_forwardHumans are able to digest amylose, but not cellulose. What structural features of these polysaccharides might be responsible for this? O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds O amylose contains only beta glycosidic bonds where cellulose contains alpha glycosidic bonds amylose contains only alpha peptide bonds where cellulose contains beta peptide bonds amylose contains only alpha glycosidic bonds where cellulose contains beta glycosidic bondsarrow_forwardThe carbonyl group in d-galactose may be isomerized from C1 to C2 by brief treatmentwith dilute base (by the enediol rearrangement, Section 23-7). The product is the C4epimer of fructose. Draw the furanose structure of the product.arrow_forwardThe reaction shows the chemical synthesis of protected lactose disaccharides. Which bromide donor would you choose to accomplish this transformation? Explain your reasoning.arrow_forwardPlease don't provide handwriting solutionarrow_forwardAn unknown disaccharide gives a positive Tollens’ test. A glycosidase hydrolyzes it to D-galactose and D-mannose. When the disaccharide is treated with methyl iodide and Ag2O and then hydrolyzed with dilute HCl, the products are 2,3,4,6-tetra-O-methylgalactose and 2,3,4-tri-O-methylmannose. Propose a structure for the disaccharide.arrow_forwardIf lactose is first hydrolyzed (by addition of sulfuric acid) into its constituent monosaccharide, and then subjected to complete methylation, what methylated products do you expect?arrow_forward(a) Figure 23-2 shows that the degradation of d-glucose gives d-arabinose, an aldopentose.Arabinose is most stable in its furanose form. Draw d-arabinofuranose.(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Drawd-ribofuranose.arrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_forwardCarbohydrates a. Compound Z is an aldopentose. If Z is oxidized with nitric acid the product is optically active. If Z undergoes one Ruff degradation and the product of that degradation is reduced to the alditol using H₂/Ni the resulting product is optically inactive. If compound Z undergoes two Ruff degradations, D-glyceraldehyde (shown below) is obtained. Draw the usual Fischer projection of Z (aldehyde at the top). (Hint: work backwards from D- glyceraldehyde.) H HIC OH CH₂OH D-Glyceraldehydearrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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