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Informationen zum Autor Peter G. M. Wuts, PhD, is a renowned organic chemist, currently working as a chemistry consultant for both the biotech and the legal community. He continues a 50-year career in academia and the pharmaceutical industry. Klappentext Integral, reliable, and comprehensive guidance for chemists performing the complex syntheses required for the formation and cleavage of protective groups Organic synthesis is the preparation and creation of organic compounds for use in natural products, pharmaceuticals, and other molecules. The synthesis of molecules having multiple functional groups often requires the use of 'protective groups' to achieve site selectivity in a chemical reaction within a molecule bearing multiple sites of reactivity. Protective groups are installed temporarily to prevent unwanted reactions at a particular site, while transforming a different functional group. Once they have served their function, they are removed to expose the original group. Without a thorough understanding of the methods required to install and remove them, the design of a synthesis of a molecule having multiple functional groups in most cases is effectively impossible. Greene's Protective Groups in Organic Synthesis, 6th Edition is the definitive compilation of protective groups, their classification, and their application in a wide array of situations. With a long tradition of comprehensive coverage, organized on the basis of the functional group in need of protection and subsequent deprotection, it is an essential reference and resource for all chemists involved in organic syntheses. Now fully updated to reflect the current state of the art, it remains an indispensable resource for generating life-changing organic products. This edition contains a new chapter on how protective groups effect reactivity and selectivity in carbohydrate chemistry. Readers of the sixth edition of Greene's Protective Groups in Organic Synthesis will also find: Methodology for planning selectivity in organic synthesesDetailed discussion of all major functional groups including ethers, amides, and phenolsA discussion of the impact of protective groups on reactivity in carbohydrates Greene's Protective Groups in Organic Synthesis is ideal for synthetic organic chemists or medicinal chemists in academia, industry - pharmaceuticals, food, agrochemicals, and biotech - or government agencies. Inhaltsverzeichnis Preface xiii Abbreviations xv Volume 1 1. The Role of Protective Groups in Organic Synthesis 1 Properties of a Protective Group 1 Historical Development 1 Development of New Protective Groups 2 Selection of a Protective Group from This Book 3 Synthesis of Complex Substances. Two Examples (As Used in the Synthesis of Himastatin and Palytoxin) of the Selection Introduction and Removal of Protective Groups 4 Synthesis of Himastatin 4 Synthesis of Palytoxin Carboxylic Acid 8 2. Protection for the Hydroxyl Group Including 12- and 13- Diols 13 Ethers 22 Substituted Methyl Ethers 30 Substituted Ethyl Ethers 78 Methoxy- Substituted Benzyl Ethers 136 Silyl Ethers 191 Migration of Silyl Groups 193 Cleavage 226 Esters 254 Proximity Assisted Deprotection for Ester Cleavage 313 Miscellaneous Esters 320 Sulfonates Sulfenates and Sulfinates as Protective Groups for Alcohols 321 Carbonates 330 Carbamate Protection of Alcohols 356 Protection for 12- and 13- Diols 359 Monoprotection of Diols 360 Cyclic Acetals and Ketals 383 Chiral Ketones 443 Cyclic Ortho Esters 444 Silyl Derivatives 452 Cyclic Carbonates 461 Cyclic Boronates 464 3. Protection for Phenols and Catechols 469 Protection for Phenols and Catechols 472
