Greene's Protective Groups in Organic Synthesis - 5th Edition

Informationen zum Autor Peter G.M. Wuts is a Distinguished Scientist at Kalexsyn, Inc. in Kalamazoo, Michigan. Klappentext An indispensable reference for any practicing synthetic organic or medicinal chemist, this book continues the tradition of Greene's as comprehensive in the overall scope of coverage, providing the most relevant and useful examples to illustrate each methodology.* Presents valuable material, on the application of protective groups in organic chemistry, that is not easily found by casual searching* Helps chemists to plan, investigate, and carry out organic syntheses in an efficient manner* Adds over 2800 new references to update since the publication of the last edition* Reviews of the prior edition: "An essential bible for the library or personal bookshelf of chemists performing complex synthesis." (CHOICE, May 2007) "...the most up-to-date compilation available...should be an integral part of all institutional libraries...it is also highly recommended that individuals...maintain their own copy..." (Journal of Medicinal Chemistry, March 8, 2007) "...continues to be a comprehensive guide to the techniques for the formation and cleavage of protective groups." (Journal of the American Chemical Society, January 31, 2007) Zusammenfassung An indispensable and comprehensive reference for synthetic organic or medicinal chemists, this book presents valuable material on the application of protective groups in organic chemistry, which is not easily found by casual searching. Each chapter is updated with new material published since the last edition, totalling over 2800 references. Inhaltsverzeichnis Preface to the Fifth Edition xi Preface to the Fourth Edition xiii Preface to the Third Edition xv Preface to the Second Edition xvii Preface to the First Edition xix Abbreviations xxi 1. The Role of Protective Groups in Organic Synthesis 1 Properties of a Protective Group 1 Historical Development 2 Development of New Protective Groups 2 Selection of a Protective Group from This Book 4 Synthesis of Complex Substances: Two Examples (As used in the Synthesis of Himastatin and Palytoxin) of the Selection Introduction and Removal of Protective Groups 5 Synthesis of Himastatin 5 Synthesis of Palytoxin Carboxylic Acid 9 2. Protection for the Hydroxyl Group Including 12- and 13-Diols 17 Ethers 26 Substituted Methyl Ethers 33 Substituted Ethyl Ethers 87 Methoxy-Substituted Benzyl Ethers 146 Silyl Ethers 201 Esters 271 Bisfluorous Chain-Type Propanoate (Bfp-OR) Ester 307 Proximity-Assisted Deprotection for Ester Cleavage 329 Miscellaneous Esters 336 Sulfonates Sulfenates and Sulfinates as Protective Groups for Alcohols 337 Carbonates 347 Carbamates 371 Protection for 12- and 13-Diols 375 Monoprotection of Diols 375 Cyclic Acetals and Ketals 385 Chiral Ketones 446 Cyclic Orthoesters 447 Silyl Derivatives 456 Cyclic Carbonates 465 Cyclic Boronates 468 3. Protection for Phenols and Catechols 472 Protection for Phenols 475 Ethers 475 Silyl Ethers 522 Esters 528 Carbonates 535 Carbamates 538 Phosphinates 540 Sulfonates 541 Protection for Catechols (12-Dihydroxybenzenes) 545 Cyclic Acetals and Ketals 545 Cyclic Esters 551 Protection for 2-Hydroxybenzenethiols 552 4. Protection for the Carbonyl Group 554 Acetals and Ketals 559 Acyclic Acetals and Ketals 559 Cyclic Acetals and Ketals 576 Chiral Acetals and Ketals 611 Dithio Acetals and Ketals 615 Cyclic Dithio Acetals and Ketals 620 Monothio Acetals and Ketals 644 Diseleno Acetals and Ketals 649 Miscellaneous D...

List of contents

Preface to the Fifth Edition xi
 
Preface to the Fourth Edition xiii
 
Preface to the Third Edition xv
 
Preface to the Second Edition xvii
 
Preface to the First Edition xix
 
Abbreviations xxi
 
1. The Role of Protective Groups in Organic Synthesis 1
 
Properties of a Protective Group 1
 
Historical Development 2
 
Development of New Protective Groups 2
 
Selection of a Protective Group from This Book 4
 
Synthesis of Complex Substances: Two Examples (As used in the Synthesis of Himastatin and Palytoxin) of the Selection Introduction and Removal of Protective Groups 5
 
Synthesis of Himastatin 5
 
Synthesis of Palytoxin Carboxylic Acid 9
 
2. Protection for the Hydroxyl Group Including 12- and 13-Diols 17
 
Ethers 26
 
Substituted Methyl Ethers 33
 
Substituted Ethyl Ethers 87
 
Methoxy-Substituted Benzyl Ethers 146
 
Silyl Ethers 201
 
Esters 271
 
Bisfluorous Chain-Type Propanoate (Bfp-OR) Ester 307
 
Proximity-Assisted Deprotection for Ester Cleavage 329
 
Miscellaneous Esters 336
 
Sulfonates Sulfenates and Sulfinates as Protective Groups for Alcohols 337
 
Carbonates 347
 
Carbamates 371
 
Protection for 12- and 13-Diols 375
 
Monoprotection of Diols 375
 
Cyclic Acetals and Ketals 385
 
Chiral Ketones 446
 
Cyclic Orthoesters 447
 
Silyl Derivatives 456
 
Cyclic Carbonates 465
 
Cyclic Boronates 468
 
3. Protection for Phenols and Catechols 472
 
Protection for Phenols 475
 
Ethers 475
 
Silyl Ethers 522
 
Esters 528
 
Carbonates 535
 
Carbamates 538
 
Phosphinates 540
 
Sulfonates 541
 
Protection for Catechols (12-Dihydroxybenzenes) 545
 
Cyclic Acetals and Ketals 545
 
Cyclic Esters 551
 
Protection for 2-Hydroxybenzenethiols 552
 
4. Protection for the Carbonyl Group 554
 
Acetals and Ketals 559
 
Acyclic Acetals and Ketals 559
 
Cyclic Acetals and Ketals 576
 
Chiral Acetals and Ketals 611
 
Dithio Acetals and Ketals 615
 
Cyclic Dithio Acetals and Ketals 620
 
Monothio Acetals and Ketals 644
 
Diseleno Acetals and Ketals 649
 
Miscellaneous Derivatives 650
 
O-Substituted Cyanohydrins 650
 
Substituted Hydrazones 654
 
Oxime Derivatives 661
 
12-Adducts to Aldehydes and Ketones 669
 
Cyclic Derivatives 674
 
Protection of the Carbonyl Group as Enolate Anions Enol Ethers Enamines and Imines 676
 
Monoprotection of Dicarbonyl Compounds 679
 
Selective Protection of alpha- and ß-Diketones 679
 
Cyclic Ketals Monothio and Dithio Ketals 684
 
5. Protection for the Carboxyl Group 686
 
Esters 692
 
General Preparation of Esters 692
 
General Cleavage of Esters 699
 
Transesterification 704
 
Enzymatically Cleavable Esters 711
 
Substituted Methyl Esters 723
 
2-Substituted Ethyl Esters 739
 
26-Dialkylphenyl Esters 768
 
Substituted Benzyl Esters 775
 
Silyl Esters 792
 
Activated Esters 796
 
Miscellaneous Derivatives 799
 
Stannyl Esters 812
 
Amides and Hydrazides 812
 
Amides 820
 
Hydrazides 825
 
Protection of Sulfonic Acids 828
 
Protection of Boronic Acids 831
 
6. Protection for the Thiol Group 837
 
Thioethers 841
 
S-Diphenylmethyl Substituted S-Diphenylmethy

Summary

An indispensable and comprehensive reference for synthetic organic or medicinal chemists, this book presents valuable material on the application of protective groups in organic chemistry, which is not easily found by casual searching. Each chapter is updated with new material published since the last edition, totalling over 2800 references.

Product details

• Authors: Peter G M Wuts, Peter G. M. Wuts, WUTS PETER G M, Wuts Peter G. M.
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Hardback
• Released: 22.12.2014
• EAN: 9781118057483
• ISBN: 978-1-118-05748-3
• No. of pages: 1400
• Dimensions: 165 mm x 245 mm x 60 mm
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, ORGANIC CHEMISTRY, Synthese, Chemie (organisch), chemistry, Organische Synthese, Industrial Chemistry, Technische u. Industrielle Chemie, Wirkstoffforschung u. -entwicklung, Drug Discovery & Development, Schutzgruppen (Chem.)