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16-58 Following is a structural formula of desosamine, a sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago. ch 3 T Desosamine Name all the functional groups in desosamine. (Chapter 10) How many stereocenters are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it? Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial. (d > Which of the alternative chair conformations for desosamine is more stable?

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Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759
BuyFind

Introduction to General, Organic a...

11th Edition
Frederick A. Bettelheim + 4 others
Publisher: Cengage Learning
ISBN: 9781285869759

Solutions

Chapter
Section
Chapter 16, Problem 16.58P
Textbook Problem

16-58 Following is a structural formula of desosamine, a

sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago.

ch3

T

Chapter 16, Problem 16.58P, 16-58 Following is a structural formula of desosamine, a sugar component of several macrolide

Desosamine

  1. Name all the functional groups in desosamine. (Chapter 10)
  2. How many stereocenters are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it?
  3. Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial.

(d > Which of the alternative chair conformations for desosamine is more stable?

Expert Solution
Interpretation Introduction

(a)

Interpretation:

All the functional groups in desosamine should be determined.

Concept Introduction:

The IPUAC name of desosamine is 3-(dimethylamino)-3,4,6-trideoxyhexose. It is mostly present in several macrolide antibiotics like erythromycin which is generally prescribed by the physician.

Explanation of Solution

Alcohols are hydroxyl derivatives of alkanes. Thus, the functional group is C-OH.

The functional group of ether is C-O-C.

Amines may be regarded as derivatives of ammonia in which one or more hydrogen atoms have been replaced by alkyl group...

Expert Solution
Interpretation Introduction

(b)

Interpretation:

How many stereocenters are present in desosamine. Determine how many stereoisomers and how many pairs of enantiomers are possible?

Concept Introduction:

The IPUAC name of desosamine is 3-(dimethylamino)-3,4,6-trideoxyhexose. It is mostly present in several macrolide antibiotics like erythromycin which is generally prescribed by the physician.

Expert Solution
Interpretation Introduction

(c)

Interpretation:

Draw the chair conformation and determine equatorial and axial group.

Concept Introduction:

The IPUAC name of desosamine is 3-(dimethylamino)-3,4,6-trideoxyhexose. It is mostly present in several macrolide antibiotics like erythromycin which is generally prescribed by the physician.

Expert Solution
Interpretation Introduction

(d)

Interpretation:

Which chair conformation is more stable.

Concept Introduction:

The IPUAC name of desosamine is 3-(dimethylamino)-3,4,6-trideoxyhexose. It is mostly present in several macrolide antibiotics like erythromycin which is generally prescribed by the physician.

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Chapter 16 Solutions

Introduction to General, Organic and Biochemistry
Show all chapter solutions
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