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Draw the structures (using chair conformations of pyranoses) of the following disaccharides.

(a) 4-O-( -D-glucopyranosyl)-D-galactopyranose

(b) -D-fructofuranosyl-尾 -D-mannopyranoside

(c) 6-O-(尾 -D-galactopyranosyl)-D-glucopyranose

Short Answer

Expert verified

(a)

4-O-(伪 -D-glucopyranosyl)-D-galactopyranose

(b)

伪 -D-fructofuranosyl-尾 -D-mannopyranoside

(c)

6-O-(尾 -D-galactopyranosyl)-D-glucopyranose

Step by step solution

01

Disaccharide

A sugar consisting of two monosaccharide unit is a disaccharide. Most common disaccharides are sucrose, lactose, maltose etc.

02

Pyranose and furanose

Pyranose is a six-membered cyclic hemiacetal while a furanose is a five-membered cyclic hemiacetal.

03

Anomers

The diastereomers resulting from cyclisation are known as anomers. They differ only in the configuration around first carbon (C1) which is referred to as the anomeric carbon (hemiacetal carbon atom).

04

Identifying  and  anomers of pyranoses α and β furanoses

For 伪 -anomer, hydroxy group (-OH) on the anomeric carbon is down (axial position) while for 尾 - anomer, hydroxy group (-OH) on the anomeric carbon is up (equatorial position). Again, for 伪 -anomer, the anomeric hydroxy (-OH) group is placed trans to the terminal -CH2OH group while for 尾 -anomer, the anomeric hydroxy (-OH) group is placed cis to the terminal -CH2OH group.

05

Structure of disaccharides

(a)

4-O-(伪 -D-glucopyranosyl)-D-galactopyranose

(b)

伪 -D-fructofuranosyl-尾 -D-mannopyranoside

(c)

6-O-(尾 -D-galactopyranosyl)-D-glucopyranose

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Most popular questions from this chapter

Some protecting groups can block two OH groups of a carbohydrate at the same time. One such group is shown here, protecting the 4-OH and 6-OH groups of 尾 -D-glucose.

(a) What type of functional group is involved in this blocking group?

(b) What did glucose react with to form this protected compound?

(c) When this blocking group is added to glucose, a new chiral center is formed. Where is it? Draw the stereoisomer that has the other configuration at this chiral center. What is the relationship between these two stereoisomers of the protected compound?

(d) Which of the two stereoisomers in part (c) do you expect to be the major product? Why?

(e) A similar protecting group, called an acetonide, can block reaction at the 2鈥 and 3鈥 oxygens of a ribonucleoside. This protected derivative is formed by the reaction of the nucleoside with acetone under acid catalysis. From this information, draw the protected product formed by the reaction.

Fructose is found in many fruits. From memory, draw fructose in

  1. the Fischer projection of the open chain.
  2. The most stable chair conformation of the most stable pyranose anomer.
  3. The Haworth projection of the most stable pyranose anomer

Draw the following monosaccharides, using chair conformations for the pyranoses and Haworth projections for the furanoses.

(a)Dmannopyranose(C2epimerofglucose)(b)Dgalactopyranose(C4epimerofglucose)(c)Dallopyranose(C3epimerofglucose)(d)Darabinofuranose(e)Dribofuranose(C2epimerofarabinose)

(a) Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.

(b) Show what happens when the product of part (a) is hydrolyzed using dilute acid.

(c) What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?

a) Draw D-allose, the C3 epimer of glucose.

b) Draw D-talose, the C2 epimer of D-galactose.

c) Draw D-idose, the C3 epimer of D-talose. Now compare your answers with Figure 23-3.

d) Draw the C4 鈥渆pimer鈥 of D-xylose. Notice that this 鈥渆pimer鈥 is actually an L-series sugar, and we have seen its enantiomer. Give the correct name for this L-series sugar.

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