Aliphatic Compounds - 2nd Edition - ISBN: 9780444898739, 9781483144658

Aliphatic Compounds

2nd Edition

Trihydric Alcohols, Their Oxidation Products and Derivatives, Penta- and Higher Polyhydric Alcohols, Their Oxidation Products and Derivatives; Saccharides, Tetrahydric Alcohols, Their Oxidation Products and Derivatives

Editors: Malcolm Sainsbury
eBook ISBN: 9781483144658
Imprint: Elsevier
Published Date: 12th March 1993
Page Count: 566
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Rodd's Chemistry of Carbon Compounds, Volume I: Aliphatic Compounds focuses on the chemistry of polyhydric alcohols and saccharides. The chemistry of polyhydric alcohols is a vast and crucially important area, not only because of the prominent roles that polyols have in their own right, but because of the way they and their modified forms are incorporated into natural products. The topics covered include the analogues, derivatives, and oxidation products of trihydric and tetrahydric alcohols; phospholipids; polyhydric alcohols and their oxidation products; synthesis, chemistry, structure and physical properties, and use in the synthesis as chiral templates and asymmetric synthesis of natural products of monosaccharides; and disaccharides and oligosaccharides. This text also discusses the applications of carbohydrates as chiral auxiliaries, templates, and starting materials in syntheses. This volume is a useful reference for students and organic chemists.

Table of Contents


List of Common Abbreviations and Symbols Used

Chapter 18. Trihydric Alcohols, Their Analogues and Derivatives and Their Oxidation Products: Trihydric Alcohols to Triketones

1. Preparation of Glycerol

2. Reactions of Glycerol

3. Use of Chiral Synthons Derived from Glycerol in Synthesis

(a) Chiral γ-Lactones

(b) The Synthesis Heteroyohimbine Alkaloid Precursors

4. Glycerides

Chapter 19. Trihydric Alcohols and Their Oxidation Products (Continued)

Dihydroxycarboxylic and Trihydroxycarboxylic Acids and Related Compounds

1. Dihydroxycarboxylic Acids

(I) Preparation of Mevalonic Acid and Mevalonolactone

(II) Biosynthesis of Isoleucine and Valine

2. Amino Hydroxy Carboxylic Acids

3. 2-Amino-2-Alkenoic Acids (Didehydroaminocarboxylic Acids)

4. Representative Amino Carboxylic Acids and Related Compounds

Chapter 20. Trihydric Alcohols and Their Oxidation Products (Continued)

Hydroxy- and Amino-Dicarboxylic Acids

Chapter 21. Phospholipids

General References

1. Synthesis of Phospholipids

(a) Halophosphate Reagents

(b) Cyclic Reagents

(c) The Cyclic Enediol Phosphoryl (CEP) Method

(d) Activating Reagents

(e) Oligonucleotide Methodology

(f) Glycidol Derivatives

(g) Semi-Synthetic Methods

2. Phospholipid Analogues

(a) Analogues Containing Sulphur

(b) Backbone Modifications

(c) Phosphonolipids

(d) Vesicles

(e) Membrane Probes

(f) Electron Transport

(g) Miscellaneous Analogues

3. Platelet-Activating Factor (PAF)

(a) Syntheses of PAF

(b) PAF Analogues

4. Phospholipase A2 Inhibitors

(a) Synthesis of PLA2 Inhibitors

Chapter 22. Polyhydric Alcohols and Their Oxidation Products

1. Introduction

2. Preparation and Synthesis of Alditols

(a) Reduction

(b) Electrolysis

(c) Enzymatic

(d) Syntheses

3. Conformation, Chelation and Chromatography

(a) Conformation and Stereochemistry

(b) Complexes and Chelation

(c) Chromatography

4. Reactions and Derivatives of the Alditols

(a) Use of Alditols in Asymmetric Synthesis

(b) Oxidation and Oxidation Products

(c) Cyclic Acetals

(d) Esters

(e) Ethers

5. Anhydroalditols

6. Deoxyalditols

7. Aminoalditols

8. Deoxynitroalditols

9. Sulphur Containing Derivatives

Chapter 23a. Monosaccharides: Synthesis, Chemistry, Structure and Physical Properties

1. Introduction

2. Synthesis of Monosaccharides

(a) Diels-Alder Types

(b) Oxirane Ring Openings

(c) Wittig Reactions

(d) Organometallic Reagents

(e) Miscellaneous Reactions

3. Amino Monosaccharides

(a) Oxirane Ring Opening

(b) Condensation Type Reaction

(c) Diels-Alder Type Constructions

(d) Miscellaneous Reactions

4. Monosaccharides Having a Phosphorus Atom in the Ring

5. Cyano Monosaccharides

6. Halides of Monosaccharides

7. Thio and Thia Monosaccharides

8. Carbocyclic Analogues of Monosaccharides

9. Chemistry of Monosaccharides

10. Structure and Physical Properties of Monosaccharides

Chapter 23b. Monosaccharides: Use in Synthesis as Chiral Templates


1. Asymmetric Reduction

(a) Asymmetric Homogeneous Hydrogenation with Transition Metal Complexes of Monosaccharide Phosphines

(b) Asymmetric Heterogeneous Hydrogenation

(c) Asymmetric Hydrosilylation

(d) Chiral Reducing Agents Derived from Monosaccharides

2. Enantioselective Alkylation Reactions

(a) Monosaccharide Derived Enolates in Enantioselective Aldol Reactions

(b) Enantioselective Alkylation of Monosaccharide Derived Carbanions

(c) Enantioselective Alkylation with Monosaccharide Electrophiles

3. Monosaccharides as Chiral Auxiliaries for Cycloaddition Reactions

(a) Asymmetric Diels-Alder Reactions

(b) Asymmetric [3 + 2] Cycloaddition Reactions with Monosaccharide Auxiliaries

(c) Asymmetric [2 + 2] Cycloadditions with Monosaccharide Auxiliaries

4. Asymmetric Carbenoid Additions with Monosaccharide Bearing Copper Catalysts

Chapter 23c. Monosaccharides: Use in the Asymmetric Synthesis of Natural Products


1. Use of Monosaccharides for the Assembly of Natural Products With Carbocyclic Ring Systems

(a) Radical Cyclisation Strategies

(b) Cycloaddition Strategies

(c) Nucleophilic Cyclisation Strategies for the Synthesis of Carbocyclic Ring Systems in Natural Products

(d) Cationic Cyclisation Strategies

2. Use of Monosaccharides for the Assembly of Molecules with Heterocyclic Rings

3. Use of Monosaccharides in the Total Synthesis of Naturally-Occurring Macrolides

Chapter 24. Disaccharides and Oligosaccharides


1. Di- and Oligosaccharides

(a) Synthesis

(b) Physical Methods

2. Disaccharides and Related Compounds

(a) Tetrosylhexoses

(b) Pentosylpentoses

(c) Pentosylhexoses, Hexosylpentoses

(d) Deoxyhexosylpentoses

(e) Deoxyhexosyldeoxyhexoses

(f) Deoxyhexosylhexoses

(g) Hexosyldeoxyhexoses

(h) Hexosylhexoses

(i) KDO-Containing Disaccharides

(j) Non-Reducing Disaccharides

(k) Nitrogen-Containing Disaccharides

(l) Uronic Acids

3. Trisaccharides and Related Compounds

(a) Neutral Sugar Containing Trisaccharides

(b) Deoxysugar-Containing Trisaccharides

(c) Nitrogen-Containing Trisaccharides

4. Tetrasaccharides and Higher Oligosaccharides

5. Sulphur-Containing Oligosaccharides

Chapter 25. Tetrahydric Alcohols, Their Analogues, Derivatives and Oxidation Products

1. Tetrahydric Alcohols

(a) Tetritols

(b) Derivatives of The Tetritols

(c) Homologous Tetrahydric Alcohols

2. Trihydroxyaldehydes and Trihydroxyketones

3. Dihydroxydiones and Their Derivatives

4. Trihydroxycarboxylic Acids

5. Dihydroxyalkanedicarboxylic Acids

6. Dioxodicarboxylic Acids

7. Tetracarboxylic Acids

(a) Alkanetetracarboxylic Acids

(b) Alkenetetracarboxylic Acids

Guide to the Index



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© Elsevier 1993
eBook ISBN:

About the Editor

Malcolm Sainsbury