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Chapter 23: Question 53 (page 1255)

Draw the following sugar derivatives.

  1. ethyl-β-D-glucopyranoside
  2. 2,3,4,6-tetra-O-ethyl-D-mannopyranose
  3. 1,3,6-tri-O-ethyl-D-fructofuranose
  4. Ethyl-2,3,4,6-tetra-O-methyl-β-D-galactopyranoside

Short Answer

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Answer :

Step by step solution

01

Diagrams of the given sugar derivates:

Pyranose is a cyclic hemiacetal form of a monosaccharide having a six-membered ring whereas pyranoside is glycoside form of pyranose. Furanose can be either hemiacetal or hemiketal and possess five-membered ring structure which consist of carbon and oxygen atoms.

2,3,4,6-tetra-O-ethyl-D-mannopyranose

1,3,6-tri-O-ethyl-D-fructofuranose

ethyl-2,3,4,6-tetra-O-methyl--D-galactopyranoside

ethyl--D-glucopyranoside

02

Naming of the sugar derivates

The carbohydrate part of the molecule is known as glycone and the -O- bridge is glycosidic oxygen. The linkage present is named in the middle of the pyranoside or furanose or pyranose sugar. Saccharide name ends with ‘ide’ or ‘ose’.

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Most popular questions from this chapter

(a) Give the products expected when (-)-erythrose reacts with HCN.

(b) What is the relationship between the products? How might they be separated?

(c) Are the products optically active? Explain.

Erwin Chargaff’s discovery that DNA contains equimolar amounts of guanine and cytosine and also equimolar amounts of adenine and thymine has come to be known as Chargaff’s rule:

G = C and A = T

(a) Does Chargaff’s rule imply that equal amounts of guanine and adenine are present in DNA? That is, does G = A?

(b) Does Chargaff’s rule imply that the sum of the purine residues equals the sum of the pyrimidine residues? That is, does A + G = C + T?

(c) Does Chargaff’s rule apply only to double-stranded DNA, or would it also apply to each individual strand if the double helical strand were separated into its two complementary strands?

Raffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose does not reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinose gives 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 is unaffected by treatment with a-galactosidase, but an α -galactosidase hydrolyzes it to D-galactose and sucrose. When raffinose is treated with dimethyl sulfate and base followed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetra-O-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the complete structures of raffinose and melibiose and give a systematic name for melibiose.

Cellulose is converted to cellulose acetateby treatment with acetic anhydride and pyridine. Cellulose acetate is soluble in common organic solvents, and it is easily dissolved and spun into fibers. Show the structure of cellulose acetate.

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 “epimer” of D-xylose. Notice that this “epimer” 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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