General Carbohydrate Method

Content: 
Methods in Carbohydrate Chemistry, Page ii
Front Matter, Page iii
Copyright, Page iv
Contributors to Volume VI, Pages xv-xviii
Preface, Page xix, ROY L. WHISTLER
Outline of volumes I–V, Pages xxi-xxiii
Errata and Additions—Volumes I–V, Pages xxv-xxvii
[1] - Gas–Liquid Chromatography of Trimethylsilyl Derivatives: Analysis of Corn Syrup, Pages 3-8, K.M. BROBST
[2] - Gas Chromatographic Estimation of Carbohydrates in Glycosphingolipids, Pages 8-13, CHARLES C. SWEELEY, ROBERT V.P. TAO
[3] - Gas–Liquid Chromatography of Trimethylsilyl Ethers of Cyclitols, Pages 14-20, F. LOEWUS, R.H. SHAH
[4] - Gas–Liquid Chromatography of Alditol Acetates, Pages 20-24, J.H. SLONEKER
[5] - Gas–Liquid Chromatography of Methylated Sugars, Pages 25-41, H.G. JONES
[6] - Qualitative Thin-Layer Chromatography, Pages 42-53, R.E. WING, J.N. BEMILLER
[7] - Quantitative Thin-Layer Chromatography, Pages 54-59, R.E. WING, J.N. BEMILLER
[8] - Preparative Thin-Layer Chromatography, Pages 60-64, R.E. WING, J.N. BEMILLER
[9] - Partition Chromatography on Ion-Exchange Resins, Pages 65-75, OLOF SAMUELSON
[10] - Determination of Carbonyl Groups with Sodium Cyanide: Total Carbonyls, Ketones and Aldehydes in Cellulose, Pages 76-81, MENACHEM LEWIN
[11] - Determination of Carbonyl Groups in Oxidized Cellulose: Oximation, Oxime Hydrolysis, and Chlorous Acid-Sodium Borohydride Methods, Pages 81-87, MIKULÁŠ PAŠTEKA
[12] - Direct Spectrophotometric Determination of Iodate following Periodate Oxidation of α-Glycol Groups: Quantitative Removal of Iodate and Periodate by Ion-Exchange Materials or by Solvent Extraction, Pages 87-93, J.X. KHYM
[13] - Determination of Formic Acid in the Periodate Oxidation of Carbohydrates, Pages 93-100, J.F. KENNEDY
[14] - Determination of Starch with Glucoamylase, Pages 100-105, P. THIVEND, CHRISTIANE MERCIER, A. GUILBOT
[15] - Use of Concanavalin A for Structural Studies, Pages 106-119, I.J. GOLDSTEIN
[16] - β-d-Allose: From D-Glucose by Oxidation of 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose and Reduction of 1,2:5,6-Di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose, Pages 123-128, J.D. STEVENS
[17] - d-Gulose: Sodium Borohydride Reduction of 3-0-Acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose, Pages 129-131, WOLFGANG MEYER ZU RECKENDORF
[18] - Aldohexofuranoses: Reduction of Aldono-1,4-lactones with Bis(3-methyl-2-butyl)borane, Pages 131-134, LEON M. LERNER
[19] - Migration of Epoxide Rings and Stereoselective Ring Opening of Acetoxyepoxides: Methyl 2,3-Anhydro-6-0-triphenylmethyl-α-D-gulopyranoside, Methyl 3-0-Acetyl-α-D-gulopyranoside, Methyl 4-0-Acetyl-α-D-arabinopyranoside, 3,4-Anhydro-α-D-arabino-pyranoside, 3,5-Anhydro-1,2-0-isopropylidene-α-D-glucofuranose, and Methyl 3,5-Anhydro-ß-D-xylofuranoside, Pages 135-141, J.G. BUCHANAN
[20] - Acetoxonium Ion Rearrangements: α-D-Idopyranose Pentaacetate, 6-Bromo-6-deoxy-α-D-idopyranose Tetraacetate, α-D-Talopyranose Pentaacetate, neo-Inositol, Pages 142-149, HANS PAULSEN
[21] - Application of the Wittig Reaction to the Synthesis of Higher Sugars: D-threo-L-galacto- and D-threo-L-ido-Octonic Acid, Pages 150-153, N.K. KOCHETKOV, B.A. DMITRIEV
[22] - Isolation of Polysaccharides from Gram-Negative Bacteria, Pages 154-157, H.E. CONRAD
[23] - Lipopolysaccharides: Preparation from Gram-Negative Bacteria, Pages 157-162, G.A. ADAMS
[24] - Teichoic Acids, Pages 162-172, A.R. ARCHIBALD
[25] - 5-Deoxy-d-xylo-hexose: Lithium Aluminum Hydride Reduction of a Tosyloxy Group, Pages 173-176, W.G. OVEREND
[26] - 6-Deoxy-d-glucose (d-Quinovose): Lithium Aluminum Hydride Reduction of Methyl 6-Chloro-6-deoxy-α-D-glucopyranoside, Pages 177-179, MICHAEL E. EVANS, FREDERICK W. PARRISH
[27] - Bromodeoxy Sugars from Epoxides: Methyl 5-O-Acetyl-3-bromo-3-deoxy-α-D-arabinofuranoside, Methyl 5-O-Acetyl-2-bromo-2-deoxy-ß-D-xylofuranoside, and Methyl 5-O-Acetyl-3-bromo-3-deoxy-ß-D-arabinofuranoside, Pages 179-182, E.J. REIST, S.H. KRUSE
[28] - Methyl 4-O-Benzoyl-6-bromo-6-deoxy-hexopyranosides, Pages 183-189, S. HANESSIAN
[29] - Chlorodeoxy Sugars via (Chloromethylene)-dimethyliminium Chloride Reactions: 6-Chloro-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-pyranose and 6-Chloro-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose, Pages 190-193, S. HANESSIAN
[30] - 6-Chloro-6-deoxy-α-d-glucose: From Methyl α-D-Glucopyranoside by Reaction with Methanesulfonyl Chloride in N, N-Dimethylformamide, Pages 193-196, MICHAEL E. EVANS, FREDERICK W. PARRISH
[31] - Deoxyfluoro Sugars via Displacement of Sulfonyloxy Groups with Tetrabutylammonium Fluoride, Pages 197-200, A.B. FOSTER, R. HEMS
[32] - Deoxyfluoro Sugars from Epoxides: 3-Deoxy-3-fluoro-D-xylose from Methyl 2,3-Anhydro-ß-D-ribofuranoside, Pages 201-205, JOHN A. WRIGHT
[33] - Substitution of Hydroxyl Groups with Iodine: Methyl 5,6-Dideoxy-5-iodo-2,3-O-isopropylidene-α-L-talofuranoside and -ß-D-allofuranoside and Methyl 4,6-Dideoxy-4,6-diiodo-3-O-methyl-2-O-p-tolylsulfonyl-α-D-galactopyranoside, Pages 205-207, N.K. KOCHETKOV, A.I. Usov
[34] - Regeneration of Amino Functions from Acetamidodeoxy Sugars, Pages 208-214, S. HANESSIAN
[35] - Displacement of the p-Tolylsulfonyloxy Group in 1,2:5,6-Di-O-isopropylidene-3-O-p-tolylsulfonyl-α-d-glucofuranose: 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose, Pages 215-217, ROY L. WHISTLER, LANDIS W. DONER
[36] - Amino Sugars via Reduction of Azides: Derivatives of 3-Amino-3-deoxy-D-glucose and 2-Amino-2-deoxy-D-altrose, Pages 218-224, A.C. RICHARDSON
[37] - Synthesis of Amino Sugars with Retention of Configuration: 4-Dimethylamino-2,3,4,6-tetradeoxy-D-erythro-hexose (Isomycamine), Pages 225-228, C.L. STEVENS, C.P. BRYANT
[38] - Amino Sugars via Displacement of Sulfonyloxy Groups with Hydrazine: Methyl 4-Amino-4,6-dideoxy-2,3-O-isopropylidene-α-L-talopyranoside and Methyl 2,6-Diacetamido-2,6-dideoxy-3,4-O-isopropylidene-α-D-allopyranoside, Pages 229-235, JIRÍ JARÝ, ALENA ZOBÁĈOVÁ
[39] - Synthesis of Amino Sugars via Oximes: Methyl 4-Amino-4,6-dideoxy-α-D-allopyranoside, Pages 235-237, C.L. STEVENS, C.P. BRYANT
[40] - Amino Sugars via Anhydro Ring Opening with Ammonia: Ammonolysis of Methyl 2,3-Anhydro-4,6-0-benzylidene-α-D-allopyranoside, Pages 238-240, JIRÍ JARÝ, KAREL ĈAPEK
[41] - Amino Sugars via Nitroolefins: 3-Amino-2,3-dideoxy-D-arabino-hexose Hydrochloridem, Pages 241-244, HANS H. BAER
[42] - Methyl 3-Deoxy-3-nitrohexopyranosides: From Methyl Glycosides Through Nitromethane Cyclization, Pages 245-249, HANS H. BAER
[43] - Amino Sugars and Amino Cyclitols via Cyclization of Dialdehydes with Nitromethane: 1,4-Diamino-1,4-dideoxy-neo-inositol, Methyl 3-Amino-3-deoxy-ß-D-gluco- and ß-D-galactopyranoside, and Methyl 3-Amino-3-deoxy-α-D-mannopyranoside Hydrochloride, Pages 250-260, F.W. LICHTENTHALER
[44] - Synthetic Approaches to cis-Diamino Sugars: Neighboring Group Reactions—N-3 and N-5 Closures, Pages 260-265, T.L. HULLAR, T. NEILSON
[45] - 2,3-Diamino-2,3-dideoxy-α-d-glucose: A trans-Diamino Sugar from Benzyl 2-Acetamido-4,6-0-benzylidene-2-deoxy-α-D-glucopyranoside by Double Inversion at C-3 via Neighboring Group Participation, Pages 266-269, WOLFGANG MEYER ZU RECKENDORF
[46] - 2,6-Diamino-2,6-dideoxy-α-d-galactose: From Methyl 2,6-Dibenzamido-2,6-dideoxy-4-O-methylsulfonyl-3-O-methyl-ß-D-glucopyranoside by Inversion at C-4 via Neighboring Group Participation, Pages 270-273, WOLFGANG MEYER ZU RECKENDORF
[47] - 2,6-Diamino-2,6-dideoxy-β-d-mannose: From Methyl 2-Benzamido-4,6-0-benzylidene-2-deoxy-α-D-altropyranoside by Inversion at C-3 via Neighboring Group Participation, Pages 274-276, WOLFGANG MEYER ZU RECKENDORF
[48] - Preparation of Aminomercapto Furanose Sugars from Dithiocarbamoyl Derivatives, Pages 277-281, LEON GOODMAN
[49] - 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl Chloride, Pages 282-285, DEREK HORTON
[50] - 5-Thio-α-d-glucopyranose: Via Conversion of a Terminal Oxirane Ring to a Terminal Thiirane Ring, Pages 286-291, ROY L. WHISTLER, W.C. LAKE
[51] - 4-Thio-d-ribofuranose: From L-Lyxose via Displacement of a p-Tolylsulfonyloxy Group with Thioacetate Anion, Pages 292-296, MIROSLAV BOBEK, ROY L. WHISTLER
[52] - Unsaturated Sugars via Cyclic Thionocarbonates, Cyclic Orthoformates, and Disulfonic Ester Intermediates: 5,6-Dideoxy-1,2-0-isopropylidene-α-D-xylo-hex-5-enofuranose, 3-0-Benzyl-5,6-dideoxy-1,2-0-isopropylidene-α-D-xylo-hex-5-enofuranose, and Methyl 4,6-0-Benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside, Pages 297-301, DEREK HORTON, J. KENETH THOMSON, CHARLES G. TINDALL JR.
[53] - 2,3-Unsaturated 3-Nitro Glycosides: Methyl 4,6-0-Benzylidene-2,3-dideoxy-3-nitro-ß-D-erythro- and ß-D-threo-hex-2-enopyranosides, Pages 302-307, HANS H. BAER
[54] - Modified Synthesis of 1-Deoxyald-1-enopyranose (2-Hydroxyglycal) Esters: Conversion of 1,2-Unsaturated Pyranoid Compounds into 2,3-Unsaturated Glycopyranosyl Derivatives, Pages 307-311, R.J. FERRIER
[55] - Oxidation of Carbohydrates by the Sulfoxide–Carbodiimide and Related Methods: Oxidation with Dicyclohexylcarbodiimide-DMSO, Diisopropylcarbodiimide-DMSO, Acetic Anhydride-DMSO, and Phosphorus Pentaoxide-DMSO, Pages 315-322, G.H. JONES, J.G. MOFFATT
[56] - Oxidation of Carbohydrates with Dimethyl Sulfoxide-Acetic Anhydride: Methyl α-D-erythro-Pentopyranosid-3-ulose, Pages 323-325, BENGT LINDBERG
[57] - Synthesis of a Ketose from a Partially Benzylated Aldose: D-threo-Pentulose from 2,3,5-Tri-O-benzyl-D-arabinofuranose, Pages 326-330, YECHIEL RABINSOHN, HEWITT G. FLETCHER JR.
[58] - Oxidation of Carbohydrates with Dimethyl Sulfoxide–Phosphorus Pentaoxide, Pages 331-336, KONOSHIN ONODERA, NAOKI KASHIMURA
[59] - Oxidation with Ruthenium Dioxide and Hypochlorite: Methyl 6-Deoxy-2,3-O-isopropylidene-α-D-ribo-hexopyrano-sid-4-ulose, Pages 337-341, C.L. STEVENS, C.P. BRYANT
[60] - Selective Catalytic Oxidations of Carbohydrates, Pages 342-347, KURT HEYNS, PETER KöLL
[61] - Unsaturated Glycopyranosiduloses: 2(S)-Methoxy-4-benzoyloxy-6(R)-benzoyloxymethyl-5,6-dihydro-2H-pyran-5-one and 2(S)-Benzoyloxymethyl-4-benzoyloxy-6(S)-methoxy-5,6-dihydro-2H-pyran-5-one, Pages 348-350, F.W. LICHTENTHALER
[62] - Oxidation of Polysaccharides with Lead Tetraacetate in Dimethyl Sulfoxide, Pages 350-352, C.T. BISHOP
[63] - 1,1-Bis(acylamido)-1-deoxyalditols, Pages 355-357, J.O. DEFERRARI, I.M.E. THIEL
[64] - Methylation of Carbohydrates with Methylsulfinyl Anion and Methyl Iodide in Dimethyl Sulfoxide: Methylation of Aerobacter aerogenes A3(S1) Capsular Polysaccharide and 3-O-α-D-Glucopyranosyluronic acid-D-mannose, Pages 361-364, H.E. CONRAD
[65] - Methylation with Diazomethane–Boron Trifluoride Etherate: 1,3,4,6-Tetra-O-acetyl-2-O-methyl-ß-D-mannopyranose and 2-O-Methyl-D-mannose, Pages 365-367, J.O. DEFERRARI, E.G. GROS, I.M.E. THIEL
[66] - Benzyl Ethers: Formation and Removal: Tri-O-benzylamylose and Methyl 4-O-Benzyl-ß-D-glucopyranoside Debenzylation via Sodium in Liquid Ammonia and via Bromination, Pages 368-372, R.E. WING, J.N. BEMILLER
[67] - 2,3,4,6-Tetra-O-benzyl-α-d-glucopyranose, Pages 373-376, C.P.J. GLAUDEMANS, HEWITT G. FLETCHER JR.
[68] - Alkylation of Monosaccharides Using Sodium Hydride, Pages 376-378, J.S. BRIMACOMBE
[69] - C-4 Substitution of Methyl d-Glucosides and Malto-oligosaccharides, Pages 378-384, R.E. WING, J.N. BEMILLER
[70] - O-Carboxymethylpachyman, Pages 384-385, B.A. STONE
[71] - Glycosyl Phosphates, Pages 389-392, DONALD L. MACDONALD
[72] - l-glycero-Tetrulose (l-Erythrulose) 1-Phosphate, Pages 393-398, C.E. BALLOU
[73] - d-altro-Heptulose (d-Sedoheptulose) 7-Phosphate: Condensation of 2-Nitroethanol and D-Ribose 5-Phosphate, Pages 398-402, BRUCE A. MCFADDEN
[74] - 1l-myo-Inositol 1-Phosphate, Pages 403-408, S.G. GERO, D. MERCIER, J.E.G. BARNETT
[75] - Phosphorylation of Starch and Cellulose with an Amine Salt of Tetrapolyphosphoric Acid, Pages 408-410, GORDON A. TOWLE, ROY L. WHISTLER
[76] - 1,2,3,4-Tetra-O-acetyl-β-d-glucopyranose and Methyl 2,3,4-Tri-O-acetyl-β-d-glucopyranoside: Sugar Derivatives with a Free Primary Hydroxyl Group, Pages 411-412, ROY L. WHISTLER, LANDIS W. DONER, MARTIN KOSIK
[77] - Use of Xanthates in Synthetic Carbohydrate Chemistry: Thionocarbonate, Chlorothioformate, Dithiocarbonate, Trithiocarbonate, and S-(Methylthio)carbonyl Derivatives, Pages 413-418, W.M. DOANE
[78] - Applications of Phenylboronic Acid in Carbohydrate Chemistry, Pages 419-426, R.J. FERRIER
[79] - Sulfation of Polysaccharides, Pages 426-429, ROY L. WHISTLER
[80] - Isolation of Sugar Nucleotides, Pages 433-435, VICTOR GINSBURG
[81] - Pyrimidine Nucleosides by the Trimethylsilyl Method: Anomeric 1-(D-Ribofuranosyl)thymines and 2-ß-D-Ribofuranosyl-as-triazine-3,5(2H,4H)-dione (6-Azauridine), Pages 436-441, T. NISHIMURA
[82] - Purine Nucleosides by the Trimethylsilyl Method: 3-Ribofuranosyluric Acid and 2-Chloro-1-(ß-D-ribofuranosy1)-5,6-dimethylbenzimidazole, Pages 441-444, T. NISHIMURA
[83] - The Hilbert–Johnson Synthesis of Pyrimidine Nucleosides: 1-(2-Deoxy-ß-D-lyxo-hexopyranosyl)thymine, Pages 445-451, W. WERNER ZORBACH
[84] - Selective Phosphorylation of Ribonucleosides: Sodium Salt of Guanosine 5′-Phosphate by the Cyanoethyl Dihydrogen Phosphate and Phosphoryl Chloride Methods, Pages 451-456, YASUO FUJIMOTO, MASAYUKI TERANISHI
[85] - Cerebrosides, Isolation, Pages 459-463, H.M. FLOWERS
[86] - Gangliosides, Isolation, Pages 464-474, L. SVENNERHOLM
[87] - Use of Mercuric Cyanide and Mercuric Bromide in the Koenigs–Knorr Reaction: Alkyl ß-D-Glucopyranosides, 2-Acetamido-2-deoxy-3-O-(ß-D-galactopyranosyl)-α-D-glucose, and 2-O-α-L-Fuco-pyranosyl-D-galactose, Pages 474-480, H.M. FLOWERS
[88] - Synthesis of Oligosaccharides by the Orthoester Method, Pages 480-486, N.K. KOCHETKOV, A.F. BOCHKOV
[89] - cis-1,2-Glycosides: Isopropyl 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside, Cholesteryl 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranoside, and L-Menthyl 2,3,4-Tri-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside, Pages 487-496, R.U. LEMIEUX, T.L. NAGABHUSHAN
[90] - Preparation of Tritiated Sugars: D-Glucose-5-3H, Dihydroxyacetone-1S-3H 3-Phosphate, D-Galactose-4-3H, 2-Deoxy-D-arabino-hexose-2-3H, Heparin-3H, and 1L-chiro-Inositol-3H, Pages 499-506, J.E.G. BARNETT
[91] - Degradation and Counting of Tritium-Containing Sugars, Pages 506-509, J.E.G. BARNETT
[92] - Determination of Molecular Weights by Osmometry, Pages 510-512, GORDON A. TOWLE
[93] - Conformational Analysis via Nuclear Magnetic Resonance Spectroscopy, Pages 513-539, BRUCE COXON
[94] - Mass Spectrometry of Carbohydrates, Pages 540-554, N.K. KOCHETKOV, O.S. CHIZHOV
Glossary, Pages 555-557
Author Index, Pages 559-583
Subject Index, Pages 584-603