ORGANIC SYNTHESIS WITH CARBOHYDRATES

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ISBN: 9781850759133 | 1850759138
Cover: Hardcover
Copyright: 2/21/2000

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This book provides a broad understanding of the use of carbohydrates in organic synthesis. Emphasis is placed on retrosynthetic analysis, with discussion of why a particular synthetic route has been chosen, and mechanistic explanations are provided for key and novel reactions. Wherever possible, the authors highlight points of general significance to organic synthesis.The volume is intensively referenced and so provides a convenient point of entry to the research literature.

PART A: STRUCTURE AND SYNTHESIS OF SACCHARIDES AND GLYCOPROTEINS

Mono- and oligosaccharides: structure, configuration and conformation

(25)

Introduction

(1)

Configuration of monosaccharides

(5)

Conformational properties of monosaccharides

(11)

Ring shapes of pyranoses and furanoses

(3)

The anomeric effect

(5)

The equilibrium composition of monosaccharides in solution

(3)

Conformational properties of oligosaccharides

(1)

Acid-catalysed glycoside bond formation and cleavage

(7)

References

(2)

Protecting groups

(30)

Introduction

(1)

Ether protecting groups

(14)

Benzyl ethers

(6)

p-Methoxybenzyl ethers

(1)

Allyl ethers

(3)

Triphenylmethyl ethers

(1)

Silyl ethers

(3)

Acetal protecting groups

(5)

Benzylidene acetals

(2)

Isopropylidene acetals

(2)

Dispirodiketal and cyclohexane-1,2-diacetal groups

(1)

Ester protecting groups

(3)

Anomeric protecting groups

(2)

Amino protecting groups

(5)

Phthalimides

(1)

Azides

(1)

References

(3)

Functionalised saccharides

(47)

General introduction

(1)

Deoxyhalogeno sugars

(9)

Introduction

(1)

Direct halogenation of alcohols

(4)

Displacement reactions

(3)

Miscellaneous methods

(2)

Unsaturated sugar derivatives

(6)

Introduction

(1)

Glycals

(3)

Isolated double bonds

(1)

6-Deoxy-hex-5-enopyranose derivatives

(2)

Deoxy sugars

(5)

Introduction

(1)

Reduction of halides, sulfonates and epoxides

(2)

Radical deoxygenation of thiocarbonyl derivatives

(2)

Amino sugars

(8)

Introduction

(1)

The preparation of amino sugars by nucleophilic displacement

(4)

Addition to glycals

(1)

Reduction of oximes

(2)

Intramolecular substitutions

(1)

Epoxy sugars

(3)

Sulfated saccharides

(2)

Introduction

(2)

O and N sulfation

(1)

Phosphorylated saccharides

(14)

Introduction

(1)

Non-anomeric sugar phosphates

(4)

Anomeric phosphates

(2)

References

(7)

Oligosaccharide synthesis

103

(52)

Introduction

103

(1)

Chemical glycosidic bond synthesis

103

(7)

Glycosyl halides

105

(2)

Trichloroacetimidates

107

(2)

Thioglycosides

109

(1)

Stereoselective control in glycosidic bond synthesis

110

(12)

Neighbouring-group-assisted procedures

111

(1)

In situ anomerisation

112

(2)

Glycosylation with inversion of configuration

114

(4)

Solvent participation

118

(2)

Intramolecular aglycon delivery

120

(2)

Preparation of 2-amino-2-deoxy-glycosides

122

(2)

Formation of glycosides of N-acetyl-neuraminic acid

124

(3)

The introduction of 2-deoxy glycosidic linkages

127

(4)

Convergent block synthesis of complex oligosaccharides

131

(4)

Chemoselective glycosylations and one-pot multistep glycosylations

135

(4)

Solid-phase oligosaccharide synthesis

139

(5)

Enzymatic glycosylation strategies

144

(11)

Glycosyl transferases

146

(2)

Glycosyl hydrolases

148

(2)

References

150

(5)

The chemistry of O- and N-linked glycopeptides

155

(20)

Introduction

155

(1)

Strategies for the chemical synthesis of glycopeptides

156

(4)

Protecting groups in glycopeptide synthesis

160

(1)

Chemical synthesis of serine O-glycoside derivatives

161

(5)

The synthesis of N-glycopeptides

166

(1)

Solution-phase and solid-phase glycopeptide synthesis

167

(4)

Enzyme-mediated glycopeptide synthesis

171

(4)

References

172

(3)

PART B: NATURAL PRODUCT SYNTHESIS FROM MONOSACCHARIDES

(-)-Echinosporin

175

(11)

Introduction

175

(1)

Smith's retrosynthetic analysis of (-)-echinosporin

175

(1)

Smith's (-)-echinosporin synthesis

176

(5)

Mechanistic analysis of some key reactions employed in the Smith (-)-echinosporin synthesis

181

(5)

References

184

(2)

(+)-Zaragozic acid C

186

(14)

Introduction

186

(1)

Carreira's retrosynthetic analysis of (+)-zaragozic acid C

186

(2)

Carreira's total synthesis of (+)-zaragozic acid C

188

(6)

Mechanistic analysis of some of the key steps in Carreira's synthesis of (+)-zaragozic acid C

194

(6)

References

198

(2)

(+)-Neocarzinostatin

200

(17)

Introduction

200

(1)

Myers' retrosynthetic planning for the synthesis of (+)-neocarzinostatin

200

(6)

Myers' total synthesis of (+)-neocarzinostatin

206

(5)

Mechanistic analysis of the key steps in Myers'(+)-neocarzinostatin synthesis

211

(6)

References

215

(2)

(+)-Castanospermine

217

(7)

Introduction

217

(1)

The Pandit retrosynthetic analysis of (+)-castanospermin

217

(1)

Pandit's total synthesis of (+)-castanospermine

218

(3)

Mechanistic analysis of the Pandit synthesis of (+)-castanospermine

221

(3)

References

222

(2)

(-)-Silphiperfolene

224

(10)

Introduction

224

(1)

The Fraser-Reid retrosynthetic analysis of (-)-silphiperfolene

224

(5)

Fraser-Reid's total synthesis of (-)-silphiperfolene

229

(3)

Mechanistic analysis of the Fraser-Reid (-)-silphiperfolene synthesis

232

(2)

References

232

(2)

(-)-Allosamizoline

234

(13)

Introduction

234

(1)

The Kuzuhara retrosynthetic analysis of (-)-allosamizoline

235

(1)

The Kuzuhara total synthesis of (-)-allosamizoline

236

(3)

Mechanistic analysis of the Kuzuhara (-)-allosamizoline synthesis

239

(1)

Simpkins' retrosynthetic strategy for (-)-allosamizoline

239

(2)

Simpkins' total synthesis of (-)-allosamizoline

241

(2)

Mechanistic analysis of some key steps in the Simpkins (-)-allosamizoline synthesis

243

(2)

Epilogue

245

(2)

References

245

(2)

(-)-Reiswigin A

247

(12)

Introduction

247

(1)

The Kim retrosynthetic analysis of (-)-reiswigin A

247

(4)

The Kim total synthesis of (-)-reiswigin A

251

(3)

Mechanistic points of interest in the (-)-reiswigin A synthesis

254

(5)

References

257

(2)

(-)-Octalactin A

259

(11)

Introduction

259

(1)

The Buszek retrosynthetic analysis of (-)-octalactin A

259

(5)

Buszek's total synthesis of (-)octalactin A

264

(1)

Items of mechanistic interest in the Buszek (-)-octalactin A synthesis

265

(5)

References

269

(1)

(-)-ACRL toxin I

270

(10)

Introduction

270

(1)

The Lichtenhaler retrosynthetic analysis of (-)-ACRL toxin I

270

(3)

Lichtenhaler's total synthesis of the (-)-ACRL toxin I

273

(4)

Items of mechanistic interest in the Lichtenhaler synthesis of the (-)-ACRL toxin I

277

(2)

Epilogue

279

(1)

References

279

(1)

(+)-Gabosine E

280

(6)

Introduction

280

(1)

The Lygo retrosynthetic analysis of (+)-gabosine E

280

(2)

The Lygo synthesis of (+)-gabosine E

282

(2)

Points of mechanistic interest in the Lygo (+)-gabosine E synthesis

284

(2)

References

285

(1)

(-)-Augustamine and (-)-amabiline

286

(6)

Introduction

286

(1)

The Pearson retrosynthetic analysis of (-)-augustamine

286

(2)

The Pearson total synthesis of (-)-augustamine

288

(2)

Pearson's synthesis of (-)-amabiline

290

(1)

Mechanistic analysis of the (-)-augustamine and (-)-amabiline syntheses

290

(2)

References

291

(1)

(-)-FK506

292

(37)

Introduction

292

(1)

The Danishefsky retrosynthetic analysis of (-)-FK506

292

(3)

The Danishefsky formal total synthesis of (-)-FK506

295

(7)

The Merck endgame used in the first total synthesis of (-)-FK506

302

(3)

Smith's retrosynthetic analysis of (-)-FK506

305

(3)

The Smith formal total synthesis of (-)-FK506

308

(9)

Items of interest in the Danishefsky and Smith total syntheses of (-)-FK506

317

(12)

References

326

(3)

(3S,5S)-5-Hydroxypiperazic acid

329

(5)

Introduction

329

(1)

The Hale retrosynthetic analysis of (3S,5S)-5-hydroxypiperazic acid

329

(2)

The Hale total synthesis of (3S,5S)-5-hydroxypiperazic acid

331

(1)

Points of mechanistic interest in the Hale (3S,5S)-5-hydroxypiperazic acid synthesis

332

(2)

References

333

(1)

Index

334

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ORGANIC SYNTHESIS WITH CARBOHYDRATES

Summary

Author Biography

Table of Contents

Supplemental Materials

FREE SHIPPING

Rent More, Save More! Use code: BBRENTAL

5% off 1 book, 7% off 2 books, 10% off 3+ books

ORGANIC SYNTHESIS WITH CARBOHYDRATES

Summary

Author Biography

Table of Contents

Supplemental Materials

Digital License