Modern Synthetic Methods In Carbohydrate Chemistry

The fields of glycochemistry and glycoscience are rich and varied and where much can be learned from Nature. As Nature is not always able to produce carbohydrates in quantities useful for not only in research but also as therapeutic agents, new ways need to be found to optimize the yield. This book presents an overview of the latest developments in the field of carbohydrates, ranging from de-novo approaches via cyclodextrin chemistry to the synthesis of such highly complex glycoconjugates as glycosphingolipids and GPI anchors. The main emphasis remains on the synthetic aspects making the book an excellent source of information for those already involved in carbohydrate chemistry, as well as for those organic chemists who are beginners in this field. Equally of interest to synthetic chemists, as well as medicinal chemists and biochemists.

The second volume in the series Carbohydrate Chemistry: Proven Synthetic Methods, Volume 2 offers a collection of synthetic procedures valuable to the practice of synthetic carbohydrate chemistry. The series takes an important and unique approach in that all described procedures have been independently verified as reliable and reproducible. With editors and contributors who are highly respected scientists in the field, this book provides a widely useful reference for both researchers and students, exploring carbohydrate chemistry from both academic and industrial points of view. The book begins with an introductory section that offers tricks and tips collected by the series editor from many years of experience working in carbohydrate laboratories. The subsequent chapters present detailed protocols on both specific synthetic transformations and the preparation of common synthetic intermediates, with figures to aid in comprehension. Procedures are described for regioselective benzylidene ring opening reactions, oxidation reactions to provide uronic acids, stereoselective alpha-glucosylation reactions, and more. Protocols for synthetic intermediates of general utility include 3,4,6-tri-O-acetyl-d-galactal, phenyl 4,6-O-benzylidene-1-thio-α-d-mannopyranoside, 1,2-anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranoside, and methyl N-acetylneuraminic acid, among many others. Each chapter presents in-depth experimental descriptions for the reported procedures, including reaction setup, reaction conditions, work-up procedures, and purification protocols. The chapters also provide detailed characterization of all products and intermediates as well as copies of the 1H NMR and 13C NMR of the described products and intermediates to indicate the purity of the obtained materials and to serve as a valuable reference for future practitioners. This book provides an important starting point to reliably access synthetic carbohydrate materials and as such offers a valuable resource for the synthetic organic chemistry community. Through the streamlined access of well-defined products it provides a thrust to the rapidly growing field of chemical glycobiology.

Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.

Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.

Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 3 compiles reliable protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. To ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a wide range of readers in the carbohydrate field, including undergraduates taking carbohydrate workshops.

Modern Methods in Carbohydrate Synthesis presents in one volume a sequence of chapters leading from classical methods through to today's newest state-of -the-art technology for oligosaccharide synthesis. It places particular emphasis on the most recent breakthroughs in the field, including emerging technologies for both oligosaccharide and glycoconjugate synthesis. Chapters describing the synthesis of increasingly important glycosidic linkage analogs, as well as the oligosaccharides containing derivatives and analogs of natural sugars are included. While chemical-synthetic methods constitute the major part of the book, completing the volume is a section on the rapidly expanding and important field of enzymatic synthesis, also covering combined chemical and enzymatic synthesis. Chapters are written by leading experts in the field. Wherever possible, methods of synthesis are provided in sufficient detail to allow the reader to implement the techniques described. More than 1700 references are provided in the 21 chapters comprising the book. This volume should provide a wealth of information to a large number of synthetic organic chemists, medicinal chemists, protein chemists, biochemists, glycobiologists and cell biologists, including students in these fields.

Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, this latest volume compiles reliable protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Key Features: Explains reliable and tested protocols for the preparation of intermediates for carbohydrate synthesis Offers a unique resource in glycosciences, compiling useful information in one reference Presents protocols that are of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops Explores synthetic carbohydrate chemistry from both the academic and industrial points of view Guarantees the reader a good, clean, reproducible experiment

Long gone are the days when synthetic publications included parallel preparative experiments to document reproducibility of the experimental protocols and when journals required such documentation. The new Proven Synthetic Methods Series addresses concerns to chemists regarding irreproducibility of synthetic protocols, lack of characterization data for new compounds, and inflated yields reported in many chemical communications—trends that have recently become a serious problem. Volume One of Carbohydrate Chemistry: Proven Synthetic Methods includes more detailed versions of protocols previously published for the synthesis of oligosaccharides, C-glycosyl compounds, sugar nucleotides, click chemistry, thioglycosides, and thioimidates, among others. The compilation of protocols covers both common and less frequently used synthetic methods as well as examples of syntheses of selected carbohydrate intermediates with general utility. The major focus of this book is devoted to the proper practice of state-of-the-art preparative procedures, including: References to the starting materials used, reaction setup, work-up and isolation of products, followed by identification and proof of purity of the final material General information regarding convenience of operation and comments on safety issues Versatile and practically useful methods that have not received deserved, long-lasting recognition or that are difficult to access from their primary sources Copies of 1D NMR spectra of compounds prepared, showing purity of materials readers can expect Exploring carbohydrate chemistry from the academic points of view, the Carbohydrate Chemistry: Proven Synthetic Methods Series provides a compendium of preparatively useful procedures checked by chemists from independent research groups.