Carbohydrate Chemistry Proven Synthetic Methods Volume 1 1st Edition by Pavol Kovac ISBN 1439866899 9781439866894

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ISBN 10: 1439866899

ISBN 13: 9781439866894 

Author: Pavol Kováč

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:

Part I: Synthetic Methods

Chapter 1: Acetolysis Of 6-Deoxysugars Controlled By Armed–Disarmed Effect
Chapter 2: NaH/Im₂SO₂-Mediated Preparation Of Hex-2- And Hex-3-Enopyranoside Enol Ethers
Chapter 3: Enhancement Of The Rate Of Purdie Methylation By Me₂S Catalysis
Chapter 4: Synthesis Of Oligosaccharides By Preactivation-Based Chemoselective Glycosylation Of Thioglycosyl Donors
Chapter 5: The Use Of Hypophosphorous Acid In Radical Chain Deoxygenation Of Carbohydrates
Chapter 6: Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator For Thioglycosides
Chapter 7: Preparation Of Glycosyl Chlorides From Glycopyranoses/Glycofuranoses Under Mild Conditions
Chapter 8: C-Glycosylation Starting From Unprotected O-Glycosides
Chapter 9: Palladium-Catalyzed Sonogashira Coupling On p-Iodophenyl α-D-Mannopyranoside
Chapter 10: Synthesis By “Click Chemistry” Of An α-D-Mannopyranoside Having A 1,4-Disubstituted Triazole As Aglycone
Chapter 11: Synthesis Of Methyl Glycuronates By Chemo- And Regioselective TEMPO/BAIB-Oxidation
Chapter 12: Synthesis Of Sugar Nucleotides: A Phosphoramidite Approach
Chapter 13: Conversion Of N-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides Into N-Alkylated 2,3-N,O-Carbonyl Glycosides
Chapter 14: TIBAL-Induced Rearrangement: Synthesis Of gem-Difluorocarbagalactose
Chapter 15: Pyranose-Fused Butenolides: An Expedient Preparation From Furanose Synthons
Chapter 16: Glycal Dimerization With High Diastereoselectivity
Chapter 17: Regioselective Debenzylation Of C-Glycosylpropene
Chapter 18: Synthesis Of Azido-Functionalized Carbohydrates For The Design Of Glycoconjugates
Chapter 19: Synthesis Of Thioglycosides And Thioimidates From Glycosyl Halides
Chapter 20: Synthesis Of Thioglycosides And Thioimidates From Peracetates

Part II: Synthetic Intermediates

Chapter 21: 2-Acetamido-4,6-O-Benzylidene-2-Deoxy-D-Glucopyranose
Chapter 22: Synthesis Of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose And 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose
Chapter 23: An Easy Access To 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose And 2,3,6-Tri-O-Benzyl-D-Glucopyranose
Chapter 24: Benzyl 2,3,6,2′,3′,6′-Hexa-O-Benzyl-β-Cellobioside
Chapter 25: One-Step Syntheses Of 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose And 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose
Chapter 26: Stereoselective Synthesis Of α-C-Sialyl Compounds
Chapter 27: Synthesis Of O-Acetylated N-Acetylneuraminic Acid Glycal
Chapter 28: Substituted Benzyl Glycosides Of N-Acetylneuraminic Acid
Chapter 29: Synthesis Of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related To 1-Deoxynojirimycin
Chapter 30: Synthesis Of 1,6-Anhydro-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose
Chapter 31: Synthesis Of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside
Chapter 32: Synthesis Of 3-C-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)prop-1-Ene
Chapter 33: Synthesis Of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)but-2-Enoate By Cross-Metathesis Reaction
Chapter 34: Preparation Of O-β-D-Galactopyranosylhydroxylamine
Chapter 35: 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
Chapter 36: Efficient Synthesis Of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronates From D-Galacturonic Acid
Chapter 37: Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate
Chapter 38: p-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside: A Useful Thioglycoside Building Block In The Synthesis Of Oligoarabinofuranosides
Chapter 39: Ethylene Dithioacetals Of Common Hexoses
Chapter 40: Preparation Of 2,6-Anhydro-Aldose Tosylhydrazones
Chapter 41: Preparation Of Exo-Glycals From (C-Glycopyranosyl) Formaldehyde Tosylhydrazone
Chapter 42: Synthesis Of O-(6-Deoxy-α- And β-L-Galactopyranosyl) Hydroxylamines (α- And β-L-Fucopyranosylhydroxylamines)
Chapter 43: Functionalization Of Terminal Positions Of Sucrose—Part I: Synthesis Of 2,3,3′,4,4′-Penta-O-Benzylsucrose And Differentiation Of The Terminal Positions (1,6,6′)
Chapter 44: 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

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Tags: Pavol Kovac, Carbohydrate, Chemistry, Proven, Synthetic, Methods, Volume 1