Carbohydrate chemistry : proven synthetic methods

Author(s)

• Kováč, Pavol

Bibliographic Information

Carbohydrate chemistry : proven synthetic methods

edited by Pavol Kováč

（Carbohydrate chemistry: proven synthetic methods / series editor Pavol Kováč）

CRC Press, c2012-

• v. 1
• v. 2
• v. 3 : hardback
• v. 4 : hardback

Note

Includes bibliographical references and index

v. 2: edited by Gijsbert van der Marel, Jeroen Codee

v. 3: edited by René Roy, Sébastien Vidal

v. 4: [edited by] Christian Vogel, Paul V. Murphy

Description and Table of Contents

Volume

v. 1 ISBN 9781439866894

Description

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.

Table of Contents

Synthetic Methods: Acetolysis of 6-Deoxysugars Controlled by Armed-Disarmed Effect. NaH/Im2SO2-Mediated Preparation of Hex-2- and Hex-3-Enopyranoside Enol Ethers. Enhancement of the Rate of Purdie Methylation by Me2S Catalysis. Synthesis of Oligosaccharides by Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors. The Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates. Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for Thioglycosides. Preparation of Glycosyl Chlorides from Glycopyranoses/Glycofuranoses under Mild Conditions. C-Glycosylation Starting from Unprotected O-Glycosides. Palladium-Catalyzed Sonogashira Coupling on p-Lodophenyl -d-Mannopyranoside. Synthesis by "Click Chemistry" of an -d-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone. Synthesis of Methyl Glycuronates by Chemo- and Regioselective TEMPO/BAIB-Oxidation. Synthesis of Sugar Nucleotides: A Phosphoramidite Approach. Conversion of N-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides into N-Alkylated 2,3-N,O-Carbonyl Glycosides. TIBAL-Induced Rearrangement: Synthesis of gem-Difluorocarbagalactose. Pyranose-Fused Butenolides: An Expedient Preparation from Furanose Synthons. Glycal Dimerization with High Diastereoselectivity. Regioselective Debenzylation of C-Glycosylpropene. Synthesis of Azido-Functionalized Carbohydrates for the Design of Glycoconjugates. Synthesis of Thioglycosides and Thioimidates from Glycosyl Halides. Synthesis of Thioglycosides and Thioimidates from Peracetates. Synthetic Intermediates: 2-Acetamido-4,6-O-Benzylidene-2-Deoxy-d-Glucopyranose. Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy- , -d-Glucopyranose and 2-Azido-4,6-O-Benzylidene-2-Deoxy- , -d-Glucopyranose. An Easy Access to 2,3,4,6-Tetra-O-Benzyl-d-Galactopyranose and 2,3,6-Tri-O-Benzyl-d-Glucopyranose. Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl- -Cellobioside. One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl- , -d-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl- , -d-Arabinofuranose. Stereoselective Synthesis of -C-Sialyl Compounds. Synthesis of O-Acetylated N-Acetylneuraminic Acid Glycal. Substituted Benzyl Glycosides of N-Acetylneuraminic Acid. Synthesis of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin. Synthesis of 1,6-Anhydro-2,3,5-Tri-O-Benzoyl- -d-Galactofuranose. Synthesis of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl- -d-Mannopyranoside. Synthesis of 3-C-(2,3,4,6-Tetra-O-Acetyl- -d-Galactopyranosyl)prop-1-Ene. Synthesis of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl- -d-Galactopyranosyl)but-2-Enoate by Cross-Metathesis Reaction. Preparation of O- -d-Galactopyranosylhydroxylamine. Synthesis of 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-d-Lyxo-Hex-1-Enitol and Its Conversion into a Hex-3-Enopyranosid-2-Ulose Analogue of Levoglucosenone. Efficient Synthesis of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl- -d-Galactopyranosid)uronates from d-Galacturonic Acid. Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio- , -d-Galactofuranosid)uronate. p-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio- -d-Arabinofuranoside: A Useful Thioglycoside Building Block in the Synthesis of Oligoarabinofuranosides. Ethylene Dithioacetals of Common Hexoses. Preparation of 2,6-Anhydro-Aldose Tosylhydrazones. Preparation of Exo-Glycals from (C-Glycopyranosyl) formaldehyde Tosylhydrazone. Synthesis of O-(6-Deoxy- - and -l-Galactopyranosyl) Hydroxylamines ( - and -l-Fucopyranosylhydroxylamines). Functionalization of Terminal Positions of Sucrose-Part I: Synthesis of 2,3,3',4,4'-Penta-OBenzylsucrose and Differentiation of the Terminal Positions (1,6,6'). Functionalization of Terminal Positions of Sucrose-Part II: Preparation of 1',2,3,3',4,4'-Hexa-O-Benzylsucrose and 6,6'-Bis-O-(2-Hydroxyethyl)-1',2,3,3',4,4'-Hexa-O-Benzylsucrose.

Volume

v. 2 ISBN 9781439875940

Description

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- -d-mannopyranoside, 1,2-anhydro-3,4,6-tri-O-benzyl- -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.

Table of Contents

Section I: Synthetic Methods. Highly Stereoselective 1,2-cis-Glycosylations Employing C-2 (S)-(Phenylthiomethyl)benzyl Ether as a Chiral Auxiliary. Regioselective Reductive Openings of 4,6-O-Benzylidene-Type Acetals Using LiAlH4-AlCl3. A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids in Carbohydrate Synthesis. Ultrasonic Energy Promoted Allylation to Generate 1-C-(2,3,4,6-Tetra-O-benzyl- -d-glucopyranosyl)prop-2-ene. Synthesis of a Multivalent Glycocyclopeptide Using Oxime Ligation. Reductive Amination Methodology for Synthesis of Primary Amines from Unprotected Synthons. General Preparation of Imidazole-1-sulfonate Esters. Regioselective Monoacylation and Monoalkylation of Carbohydrates Catalyzed by a Diarylborinic Ester. The Synthesis of Carbamates from Alkenylamines. Hydrolysis of Thioglycosides Using Anhydrous N-Iodosuccinimide (NIS) and Trifluoroacetic Acid (TFA). Highly Diastereoselective Construction of l-Heptosides by a Sequential Grignard Addition/Fleming-Tamao Oxidation. Synthesis of Fluorinated Exo-glycals Mediated by Selectfluor. A Direct and Stereospecific Approach to the Synthesis of -Glycosyl Thiols. Efficient Microwave-Assisted Synthesis of 1',2,3,3',4,4',6-Hepta-O-benzyl-sucrose and 1',2,3,3',4,4'-Hexa-O-benzylsucrose. Section II: Synthetic Intermediates. Oligosaccharide-Salicylaldehyde Derivatives as Precursors of Water-Soluble, Biocompatible Anion Receptors. Allyl 3,4,6-Tri-O-Benzyl- -d-Mannopyranoside. Synthesis of a Spacer-Armed 6'-Sialyl-N-Acetyllactosamine. Synthesis of -(1 3)-mannobiose. Phenyl 4,6-O-Benzylidene-1-thio- -d-mannopyranoside. Synthesis of 1,3,4,6-Tetra-O-acetyl- -d-glucopyranose Revisited. Synthesis of 4,6-O-Benzylidene Acetals of Methyl -d-Glucopyranoside, Ethyl 1-Thio- -d-gluco- and Galactopyranoside. Synthesis of -N-Acetylneuraminic Acid Methyl Glycoside. Synthesis of Ammonium 3-Deoxy-d-manno-oct-2-ulopyranosylonate (Ammonium Kdo). Synthesis and Characterization of Tetra-O-propargyl Pentaerythritol. Improved Synthesis of Ethyl (2,3,4,6-Tetra-O-acetyl- -d-galactopyranosyl)-(1 3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido- -d-glucopyranoside. Synthesis of -d-Galactofuranosyl Phosphate. Synthesis of 1,2 4,5-Di-O-(3,3-pentylidene)arabitol via Kinetic Acetal Formation. 1,2-Anhydro-3,4,6-tri-O-benzyl- -d-mannopyranose. Synthesis of Glucosyl C-1 Dihalides from Tetra-O-acetyl- -d-glucopyranosyl Chloride. Synthesis of 3,4,6-Tri-O-acetyl-d-galactal. Efficient Synthesis of Hepta-O-acetyl- -lactosyl Azide via Phase Transfer Catalysis. Synthesis of 2,3,4,6-Tetra-O-acetyl- -d-mannopyranosyl Azide. Synthesis of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio- -d-galactopyranoside. An Alternative, Large-Scale Synthesis of 1,2 5,6-Di-O-isopropylidene- -d-ribo-hex-3-ulofuranose.

Volume

v. 3 : hardback ISBN 9781466583573

Description

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.

Table of Contents

Synthetic Methods. Synthetic Intermediates.

Volume

v. 4 : hardback ISBN 9781498726917

Description

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.

Table of Contents

Foreword Introduction Editors Series Editor Contributors Section I Synthetic Methods Chapter 1 Picoloyl-Protecting Group in Oligosaccharide Synthesis: Installation, H-Bond-Mediated Aglycone Delivery (HAD), and Selective Removal Michael P. Mannino, Jagodige P. Yasomanee, Alexei V. Demchenko, and Venukumar Patteti Chapter 2 Monomethoxytrityl (MMTr) as an Efficient S-Protecting Group in the Manipulation of Glycosyl Thiols Raymond Smith, Xiangming Zhu, and Elena Calatrava-Perez Chapter 3 One-Step Inversion of Configuration of a Hydroxy Group in Carbohydrates Shino Manabe and Markus Blaukopf Chapter 4 Formation and Cleavage of Benzylidene Acetals Catalyzed by NaHSO4 SiO2 Lifeng Sun, Xin-Shan Ye, and Xingdi Wang Chapter 5 Thiodisaccharides by Photoinduced Hydrothiolation of 2-Acetoxy Glycals Daniel Eszenyi, Laszlo Lazar, Aniko Borbas, and Ruairi O. McCourt Chapter 6 One-Step Preparation of Protected N-tert-Butanesulfinyl d-ribo and d-xylo Furanosylamines from Related Sugar Hemiacetals Chloe Cocaud, Cyril Nicolas, Olivier R. Martin, and Jerome Desire Chapter 7 An Alternative Preparation of Azides from Amines via Diazotransfer with Triflyl Azide Yuqian Ye, Xin-Shan Ye, and Xingdi Wang Chapter 8 Simple Preparation of Dimethyldioxirane and Its Use as an Epoxidation Agent for the Transformation of Glycals to Glycosyl Phosphates Katharina Kettelhoit, Daniel B. Werz, Aniruddha Sasmal, Xinyu Liu, and Philipp Gritsch Chapter 9 Preparation of Glycosyl Bromides of -d-Gluco-hept-2-ulopyranosonic Acid Derivatives Veronika Nagy, Katalin Czifrak, Laszlo Juhasz, Laszlo Somsak, and Olena Apelt Chapter 10 Preparation of 2,6-Anhydro-hept-2-enonic Acid Derivatives and Their 3-Deoxy Counterparts Sandor Kun, Szabina Deak, Katalin Czifrak, Laszlo Juhasz, Laszlo Somsak, and Olena Apelt Section II Synthetic Intermediates Chapter 11 Synthesis of 4-Nitrophenyl -d-galactofuranoside: A Useful Substrate for -d-Galactofuranosidases Studies Carla Marino, Santiago Poklepovich Caridea, Rosa M. de Lederkremer, and Sydney Villaume Chapter 12 Synthesis of Benzoylated -d-Glucosamine Derivatives Claudia Di Salvo, Karen A. Fox, Paul V. Murphy, and Jens Langhanki Chapter 13 Synthesis of 3,4,6-Tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)- -d-glucopyranose Vimal K. Harit, Namakkal G. Ramesh, and Srinivasa-Gopalan Sampathkumar Chapter 14 A Convenient Synthesis of 3,4-Di-O-acetyl-d-rhamnal (3,4-Di-O-acetyl-6-deoxy-d-glucal) Jessica N. Spradlin, Dina Lloyd, Clay S. Bennett, and Chao Liang Chapter 15 One-Pot Synthesis of 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy- -d-glucopyranose Using Anomeric O-Acylation Sergey S. Pertel, Elena S. Kakayan, Sergey A. Seryi, and Anthony W. McDonagh Chapter 16 1,2,3,5,6-Penta-O-tert-butyl(dimethyl)silyl- -d-galactofuranose: A Versatile Glycosylating Agent for Galactofuranosylation Diego Gonzalez-Salas, Carla Marino, and Monica Guberman Chapter 17 Per-O-benzoyl-1,2-O-benzylidene derivatives of Pyranoses and Furanoses-Versatile Building Blocks for Oligosaccharide Synthesis Polina I. Abronina, Alexander I. Zinin, Nikita M. Podvalnyy, Leonid O. Kononov, and Sandip Pasari Chapter 18 Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy- , -dglucopyranose Using the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller Chapter 19 Synthesis of Methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy- -and -d-glucopyranosides Alexander S. Henderson, M. Carmen Galan, and Carlo Pifferi Chapter 20 Ring-Opening of Benzylated Gluconolactone to Access Useful Gluconamide Conjugates Sarah Roy, Vincent Denavit, Tze Chieh Shiao, and Denis Giguere Chapter 21 A Multigram Synthesis of Phenyl 2-azido-3-O-benzyl-4,6-Obenzylidene-2-deoxy-1-thio- -d-mannopyranoside Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Zhen Wang Chapter 22 Preparation and Characterization of 6-Azidohexyl 2,3,4,6-tetra-O-acetyl- -d-glucopyranoside Divya Kushwaha, Pavol Kovac, and Marek Barath Chapter 23 Synthesis of (2S, 3S, 4S)-2,3,4-Tri-O-benzyl-5-bromopentanenitrile Michal Malik, Slawomir Jarosz, and Anna Zawisza Chapter 24 Simplifying Access to 3,4-Di-O-acetyl-1,5 anhydro-2,6-dideoxy-d-lyxo-hex-1-enitol (3,4-Di-O-acetyl-d-fucal) Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Satsawat Visansirikul Chapter 25 2-Chloroethyl and 2-Azidoethyl 2,3,4,6-tetra-O-acetyl- -dgluco-and -d-galactopyranosides Andrew Reddy, Jessica Ramos-Ondono, Lorna Abbey, Trinidad Velasco-Torrijos, and Thomas Ziegler Chapter 26 Synthesis of Heptakis(6-O-tert-butyldimethylsilyl) cyclomaltoheptaose Juan M. Casas-Solvas, Antonio Vargas-Berenguel, and Milo Malanga Chapter 27 Sodium d-galactonate, d-Galactono-1,4-lactone, and Synthetically Useful Methyl d-galactonates Veronica Rivas, Adriana A. Kolender, Oscar Varela, and Gilbert Duhirwe Chapter 28 Synthesis of a 3,6-Orthogonally-Protected Mannopyranoside Building Block Sarah Roy, Vincent Denavit, Danny Laine, Denis Giguere, and Julia Meyer Chapter 29 Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(bis-methoxycarbonyl) methyl]- -d-glucopyranoside Prashant Pavashe, Tukaram Pimpalpalle, Torsten Linker, and Laszlo Juhasz Chapter 30 Fluorine-Containing Carbohydrates: Synthesis of 6-Deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene- -d-galactopyranose Vincent Denavit, Danny Laine, Denis Giguere, and Guillaume Le Heiget Chapter 31 A Facile Synthesis of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trifluoroacetamido- -d-glucopyranose Nikita M. Podvalnyy, Yakov V. Voznyi, Alexander I. Zinin, Polina I. Abronina, Leonid O. Kononov, and Salvatore G. Pistorio Chapter 32 An Expeditious Route to an HO-4 Free d-GalNAc Building Block from d-GlcNAc Francisco Santoyo-Gonzalez, Fernando Hernandez-Mateo, F. J. Lopez-Jaramillo, and Clara Uriel Chapter 33 Improved Synthesis of 3-(2-Deoxy- -d-erythro-pentofuranos-1-yl) prop-1-ene Heike Wachtler, Dilver Pena Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk Chapter 34 Improved Synthesis of 3-( -d-Ribofuranos-1-yl) prop-1-ene Heike Wachtler, Dilver Pena Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk Chapter 35 3-Azidopropyl 2-Acetamido-2-deoxy- -d-glucopyranoside Jean-Baptiste Farcet, Anna Christler, Paul Kosma, and Mihaly Herczeg Chapter 36 Large-Scale Synthesis of 2,3,4,6-Tetra-O-benzyl-1-deoxynojirimycin Damien Hazelard, Mathieu L. Lepage, Jeremy P. Schneider, Maeva M. Pichon, Philippe Compain, and Fabien Massicot Chapter 37 Synthesis of Indol-3-yl Glucuronides for Monitoring Glucuronidase Activity Stephan Boettcher, Christian Czaschke, Joachim Thiem, and Mauro Pascolutti Chapter 38 Preparation of 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-d-glycero-dgulo-heptonimidamide Eszter Szennyes, Eva Bokor, Attila Kiss, Laszlo Somsak, and Yoann Pascal Chapter 39 Allyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido- -dglucopyranoside Yann Le Guen, Pierre Chassagne, Guillaume Le Heiget, Dominique Urban, and Laurence A. Mulard Chapter 40 1,2-Bis (diphenylphosphano) Ethane (DPPE)-Mediated Synthesis of Glycosyl Amides David P. Temelkoff, Peter Norris, and Adele Gabba Index

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Details

• NCID: BB10669409
• ISBN:
  • 9781439866894
  • 9781439875940
  • 9781466583573
  • 9781498726917
• LCCN: 2011010495
• Country Code: us
• Title Language Code: eng
• Text Language Code: eng
• Place of Publication: Boca Raton, FL
• Pages/Volumes: v.
• Size: 25 cm
• Classification:
  • LCC : QD322.S95
  • DC22 : 547/.27
• Subject Headings:
  • LCSH : Carbohydrates -- Synthesis
• Parent Bibliography ID:
  • BB10669293