Preparative Carbohydrate Chemistry

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ISBN: 9780824798024 | 0824798023
Cover: Hardcover
Copyright: 1/2/1997

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Detailing commonly used methods and procedures, this reference discusses the reactions and derivative forms of carbohydrates. It covers the formation, cleavage, and reactions of derivatives and illustrates bond-forming reactions of SN2 types, free radicals, chain extensions, and branching. The contents include: sugar derivatives; selected reactions in carbohydrate chemistry; chemical synthesis of oligosaccharides and O-and N -glycosyl compounds; enzymatic synthesis of sialic acid, KDO, and related deoxyulosonic acids, and of oligosaccharides; synthesis of -glycosyl compounds; carbocycles from carbohydrates; and total synthesis of sugars from non-sugars.

Preface

iii

(8)

Contributors

PART I SUGAR DERIVATES

(84)

Stephen Hanessian

1. Synthesis of Isopropylidene, Benzylidene, and Related Acetals

(32)

Pierre Calinaud

Jacques Gelas

I. Introduction

(3)

II. Methods

(9)

III. Experimental Procedures

(13)

References

(7)

2. Dialkyl Dithioacetals of Sugars

(18)

Derek Horton

Peter Norris

I. Introduction

(3)

II. Methods

(4)

III. Experimental Procedures

(7)

References

(3)

3. Regioselective Cleavage of O-Benzylidene Acetals to Benzyl Ethers

(16)

Per J. Garegg

I. Introduction

(3)

II. Regioselective Reductive Cleavage of O-Benzylidene Acetals to Benzyl Ethers

(4)

III. Mechanistic Considerations

(1)

IV. Experimental Procedures

(3)

References

(4)

4. Selective O-Substitution and Oxidation Using Stannylene Acetals and Stannyl Ethers

(16)

Serge David

I. Introduction

(1)

II. Methods

(5)

III. Experimental Procedures

(7)

References

(3)

PART II SELECTED REACTIONS IN CARBOHYDRATE CHEMISTRY

(178)

Stephen Hanessian

5. SN2-Type Halogenation and Azidation Reactions with Carbohydrate Triflates

(18)

Edith R. Binkley

Roger W. Binkley

I. Triflate Synthesis and Reactivity

(2)

II. Introducing Azido and Halogeno Groups by Triflate Displacement

(3)

III. Reactions of Carbohydrate Triflates

(3)

IV. Carbohydrate Imidazolylsufonates

(1)

V. Experimental Procedures

(5)

References

102

(3)

6. Direct Halogenation of Carbohydrate Derivates

105

(22)

Walter A. Szarek

Xianqi Kong

I. Introduction

106

(1)

II. General Methods for the Direct Halogenation of Alcohols

107

(9)

III. Experimental Procedures

116

(7)

References

123

(4)

7. Nucleophilic Displacement Reactions of Imidazole-1-Sulfonate Esters

127

(24)

Jean-Michel Vatele

Stephen Hanessian

I. Introduction

127

(3)

II. Methods

130

(6)

III. Experimental Procedures

136

(9)

References

145

(6)

8. Free Radical Deoxygenation of Thiocarbonyl Derivatives of Alcohols

151

(22)

D. H. R. Barton

J. A. Ferreira

J. C. Jaszberenyi

I. Introduction

151

(2)

II. Methods

153

(4)

III. Experimental Procedures

157

(11)

Notes and References

168

(5)

9. Thiazole-Based One-Carbon Extension of Carbohydrate Derivatives

173

(34)

Alessandro Dondoni

Alberto Marra

I. Introduction

174

(1)

II. Methods

174

(14)

III. Experimental Procedures

188

(8)

References

196

(11)

10. Selected Methods for Synthesis of Branched-Chain Sugars

207

(56)

Yves Chapleur

Francoise Chretien

I. Introduction

207

(4)

II. Methods

211

(29)

III. Experimental Procedures

240

(12)

References

252

(11)

PART III CHEMICAL SYNTHESIS OF O- AND N-GLYCOSYL COMPOUNDS, AND OF OLIGOSACCHARIDES

263

(204)

Stephen Hanessian

11. O- and N-Glycopeptides: Synthesis of Selectively Deprotected Building Blocks

265

(18)

Horst Kunz

I. Introduction

265

(3)

II. Methods

268

(5)

III. Experimental Procedures

273

(6)

References

279

(4)

12. Oligosaccharide Synthesis with Trichloroacetimidates

283

(30)

Richard R. Schmidt

Karl-Heinz Jung

I. Introduction

283

(6)

II. The Trichloroacetimidate Method

289

(7)

III. Experimental Procedures

296

(12)

References and Notes

308

(5)

13. Oligosaccharide Synthesis from Glycosyl Fluorides and Sulfides

313

(26)

K. C. Nicolaou

Hiroaki Ueno

I. Introduction

314

(1)

II. Methods

314

(15)

III. Experimental Procedures

329

(7)

References

336

(3)

14. Oligosaccharide Synthesis by n-Pentenyl Glycosides

339

(18)

Bert Frase-Reid

Robert Madsen

I. Introduction

339

(2)

II. Methods

341

(7)

III. Experimental Procedures

348

(6)

References and Notes

354

(3)

15. Chemical Synthesis of Sialyl Glycosides

357

(24)

Akira Hasegawa

Makoto Kiso

I. Introduction

358

(1)

II. Regio- and a-Stereoselective Sialyl Glycoside Syntheses Using Thioglycosides of Sialic Acids in Acetonitrile

359

(5)

III. Applications to Systematic Synthesis of Gangliosides and Sialyloligosaccharides

364

(6)

IV. Experimental Procedures

370

(5)

References

375

(6)

16. Glycoside Synthesis Based on the Remote Activation Concept: An Overview

381

(8)

Stephen Hanessian

I. Introduction

381

(1)

II. The Challenges of the Glycosidic Bond

382

(1)

III. The Remote Activation Concept

383

(3)

IV. New Generations of Glycosyl Donors

386

(1)

References

387

(2)

17. Glycoside and Oligosaccharide Synthesis with Unprotected Glycosyl Donors Based on the Remote Activation Concept

389

(24)

Boliang Lou

Gurijala V. Reddy

Heng Wang

Stephen Hanessian

I. Introduction

390

(1)

II. Glycoside and Oligosaccharide Synthesis Using 3-Methoxy-2-pyridyloxy (MOP) O-Unprotected Glycosyl Donors

391

(7)

III. Experimental Procedures

398

(12)

References

410

(3)

18. Oligosaccharide Synthesis by Remote Activation: O-Protected 3-Methoxy-2-pyridyloxy (MOP) Glycosyl Donors

413

(18)

Boliang Lou

Hoan Khai Huynh

Stephen Hanessian

I. Introduction

414

(1)

II. O-Protected 3-Methoxy-2-pyridyloxy Glycosyl Donors

415

(4)

III. Applications to the Synthesis of T Antigen and Sialyl Lex

419

(3)

IV. Experimental Procedures

422

(5)

References

427

(4)

19. Oligosaccharide Synthesis by Remote Activation: O-Protected Glycosyl 2-thiopyridylcarbonate Donors

431

(18)

Boliang Lou

Hoan Khai Huynh

Stephen Hanessian

I. Introduction

432

(2)

II. Methods: Glycosyl 2-thiopyridylcarbonates (TOPCAT) as Glycosyl Donors

434

(5)

III. Experimental Procedures

439

(8)

References

447

(2)

20. Oligosaccharide Synthesis by Selective Anomeric Activation with MOP- and TOPCAT-Leaving Groups

449

(18)

Boliang Lou

Elisabeth Eckhardt

Stephen Hanessian

I. Introduction

450

(7)

II. Experimental Procedures

457

(7)

References

464

(3)

PART IV ENZYMATIC SYNTHESIS OF SIALIC ACID, KDO, AND RELATED DEOXYULOSONIC ACIDS, AND OF OLIGOSACCHARIDES

467

(38)

Stephen Hanessian

21. Enzymatic Synthesis of Carbohydrates

469

(16)

Claudine Auge

Christine Gautheron-Le Narvor

I. Introduction

469

(2)

II. Methods

471

(7)

III. Experimental Procedures

478

(4)

References

482

(3)

22. Oligosaccharide Synthesis by Enzymatic Glycosidation

485

(20)

Wolfgang Fitz

Chi-Huey Wong

I. Introduction

486

(1)

II. Enzymatic Glycosidation

486

(8)

III. Experimental Procedures

494

(8)

References

502

(3)

PART V SYNTHESIS OF C-GLYCOSYL COMPOUNDS

505

(38)

Stephen Hanessian

23. C-Glycosyl Compounds from Free Radical Reactions

507

(20)

Bernd Giese

Heinz-Georg Zeitz

I. Introduction

507

(3)

II. Intermolecular Methods

510

(6)

III. Intramolecular Methods

516

(1)

IV. Experimental Procedures

517

(7)

References

524

(3)

24. Synthesis of Glycosylarenes

527

(16)

Keisuke Suzuki

Takashi Matsumoto

I. Introduction

528

(2)

II. Methods

530

(5)

III. Experimental Procedures

535

(6)

References

541

(2)

PART VI CARBOCYCLES FROM CARBOHYDRATES

543

(50)

Stephen Hanessian

25. Functionalized Carbocylic Derivatives from Carbohydrates: Free Radical and Organometallic Methods

545

(24)

T. V. RajanBabu

I. Introduction

546

(1)

II. Cyclopentanes

546

(8)

III. Cyclohexanes

554

(1)

IV. Functionalized Carbocylic Compounds via Organometallic Methods

555

(3)

V. Experimental Procedures

558

(7)

References and Notes

565

(4)

26. The Conversion of Carbohydrates to Cyclohexane Derivatives

569

(24)

Robert J. Ferrier

I. Introduction

570

(1)

II. Methods

571

(14)

III. Experimental Procedures

585

(5)

References

590

(3)

PART VII TOTAL SYNTHESIS OF SUGARS FROM NONSUGARS

593

(44)

Stephen Hanessian

27. Total Synthesis of Amino Sugars

595

(20)

Janusz Jurczak

I. Introduction

595

(1)

II. Methods

596

(5)

III. Experimental Procedures

601

(10)

References

611

(4)

28. Total Synthesis of Sugars

615

(22)

Aleksander Zamojski

I. Introduction

615

(2)

II. Methods

617

(5)

III. Experimental Procedures

622

(12)

References and Notes

634

(3)

Index

637

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Preparative Carbohydrate Chemistry

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