Carbohydrates / edited by Helen M. I. Osborn.

Format:

Book

Contributor:

Osborn, Helen M. I.

Series:

Best synthetic methods series.

Best synthetic methods series

Language:

English

Subjects (All):

Carbohydrates--Synthesis.

Carbohydrates.

Physical Description:

xxii, 430 pages : illustrations ; 23 cm.

Edition:

First edition.

Place of Publication:

Amsterdam ; Boston : Academic, 2003.

Summary:

In the past, carbohydrates were considered to be solely of use for energy storage, and as skeletal components. In recent years the study of carbohydrates within biological systems has illustrated that they are involved in a number of fundamental biological functions such as cell-cell recognition and cell-external-agent interactions. Therefore the view that carbohydrates are of limited importance within biological systems has been challenged and renewed interest into the science of 'Glycobiology' has emerged. In order for the roles of carbohydrates to be thoroughly analysed and assessed, glycobiologists require access to defined target carbohydrates in useful quantities. Thus carbohydrates and glycoconjugates are now recognized as important targets for total synthesis programmes and its is essential to develop efficient regio- and stereoselective methods for the synthesis of carbohydrates. Whilst carbohydrates can sometimes be isolated from natural sources, synthetic strategies often offer the advantage of allowing access to larger quantities of material as well as entry to analogues of the natural carbohydrates. Each chapter in this book details a particular theme associated with carbohydrate synthesis. A brief review of the subject area is provided, but the emphasis in all cases is on describing efficient practical methods to effect the transformations described. The book is of interest as general supplementary reading and as a reference book for use in organic chemistry research laboratories. It is also appropriate as a supplementary text and reference book for university courses and for practical classes on synthetic organic chemistry.

Contents:

Chapter 1 An Introduction to Carbohydrate Synthesis / Helen Osborn 1

1.1 Biological roles of carbohydrates 1

1.2 Synthesis of carbohydrates 5

Chapter 2 Selective Hydroxyl Protection and Deprotection / Jeremy Robertson, Petra M. Stafford 9

2.2 Hydroxyl group reactivity 10

2.3 Ethers 11

2.4 Esters 22

2.5 Carbonates 28

2.6 Acetals 29

2.7 Experimental procedures 33

Chapter 3 Synthesis and Activation of Carbohydrate Donors: Acetates, Halides, Phenyl selenides and Glycals / Benjamin G. Davis, David Chambers, Ian Cumpstey, Robert France, David Gamblin 69

3.2 Acetates 69

3.3 Halides 76

3.4 Phenyl selenides 95

3.5 Glycals 109

Chapter 4 Synthesis and Activation of Carbohydrate Donors: Thioglycosides and Sulfoxides / K.P. Ravindranathan Kartha, Robert A. Field 121

4.2 Thioglycosides 121

4.3 Sulfoxides 137

Chapter 5 Synthesis and Activation of Carbohydrate Donors: Acetimidates, n-Pentenyl and Vinyl Glycosides / Antony J. Fairbanks, Christopher M.P. Seward 147

5.1 The trichloroacetimidate method 148

5.2 Use of n-pentenyl glycosides as glycosyl donors 165

5.3 Use of vinyl glycosides as glycosyl donors 181

Chapter 6 Modern Glycosidation Methods: Tuning of Reactivity / Jorg Pietruszka 195

6.2 Influence of protecting groups 197

6.3 Influence of leaving group 205

Chapter 7 Modern Glycosidation Methods: Orthogonal Glycosidation / Jorg Pietruszka 219

7.2 Orthogonal glycosidations 220

Chapter 8 The Stereoselective Synthesis of [beta]-Mannosides / Seth C. Ennis, Helen M.I. Osborn 239

8.1 The natural occurrence of [beta]-mannosides 239

8.2 Problems associated with [beta]-mannoside synthesis 241

8.3 Synthetic methods 242

Chapter 9 Synthesis of Sialic Acid Containing Carbohydrates / Hiromune Ando, Hideharu Ishida, Makoto Kiso 277

9.2 Sialic acid donors 278

9.3 Sialylation in oligosaccharide synthesis 289

Chapter 10 The Synthesis of Glycosyl Amino Acids / Philip G. Evans, Natasha Gemmell, Helen M.I. Osborn 311

10.2 O-Glycosylamino acids and O-glycopeptides 311

10.3 N-Glycosylamino acids and N-glycopeptides 317

10.4 Solid phase synthesis of N- and O-glycosylamino acids and N- and O-glycopeptides 322

10.6 Experimental procedures 323

Chapter 11 The Synthesis of C-linked Glycosides / Paul Meo, Helen M.I. Osborn 337

11.2 Synthetic methods 339

Chapter 12 The Uses of Glycoprocessing Enzymes in Synthesis / Benjamin G. Davis, Susan M. Hancock 385

12.2 Glycosidases 387

12.3 Glycosyltransferases 413.

Notes:

Includes bibliographical references and index.

ISBN:

0123120853

OCLC:

51528744