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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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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

Question. (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. Draw D-ribofuranose.

(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. Draw D-ribofuranose.

Which of the sugars mentioned in Problem 23-53 and 23-54 are reducing sugars? Which ones undergo mutarotation?

Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B also reacts with warm nitric acid to give an optically active aldaric acid, but A reacts to give an optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, which gives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D is degraded to (+)-glyceraldehyde. Deduce the structures of sugars A,B,C and D, and use Figure 23-3 to determine the correct names of these sugars.

When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of the hydrolysate is found to be tagatose. The following information is known about tagatose:

(1) Molecular formula C6H12O6

(2) Undergoes mutarotation.

(3) Does not react with bromine water.

(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.

(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives 1,3,4,5-tetra-O-methyltagatose.

(a) Draw a Fischer projection structure for the open-chain form of tagatose.

(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose.

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