Advances in Carbohydrate Chemistry 6

Artikelnummer 10123748

CONTENTS CONTRIBUTORS TO VOLUME 6 v EDITORS' PREFACE vii Obituary of Walter Norman Haworth BY E. L. HIRST, Chemistry Department, The University, Edinburgh, Scotland 1 The Methyl Ethers of D-Galactose BY D. J. BELL, The University of Cambridge, Cambridge, England I. Introduction 11 II. Starting-materials for Preparing Tetramethyl Derivatives 12 III. Starting-materials for Preparing Trimethyl Derivatives 12 IV. Starting-materials for Preparing Dimethyl Derivatives 13 V. Starting-materials for Preparing Monomethyl Derivatives 14 VI. Monomethyl-D-Galactoses 14 VII. Dimethyl-D-Galactoses 16 VIII. Trimethyl-D-Galactoses 19 IX. Tetramethyl-D-Galactoses 22 The Synthesis of Oligosaccharides BY W. L. EVANS, Ohio State University, Columbus, Ohio, D. D. REYNOLDS, Eastman Kodak Company, Rochester, New York, AND E. A. TALLEY, Eastern Regional Research Laboratory, U. S. Department of Agriculture, Philadelphia, Pennsylvania I. Introduction 27 II. Historical Development 31 III. Reaction Type 35 IV. Conclusion 65 V. Table of Glycosyl Halides 66 VI. Table of Compounds of Alcoholic Type 67 VII. Table of Oligosaccharides 70 The Formation of Furan Compounds from Hexoses BY F. H. NEWTH, Department of Chemistry, University College of North Wales, Bangor, North Wales I. Introduction 83 II. Furan Compounds Derived from Hexoses 84 III. Furan Derivatives from Hexose Acids 89 IV. Possible Mechanisms of Formation of Furan Derivatives 91 V. 5-Hydroxymethylfurfural 95 ix Cuprammonium-Glycoside Complexes BY RICHARD E. REEVES, Southern Regional Research Laboratory, Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture, New Orleans, Louisiana I. Introduction 108 II. The Cuprammonium-Glycol Reaction 109 III. Spatial Requirements for Complexing 110 IV. Correlations between Reaction with Cuprammonium and Other Reactions of Carbohydrates 113 V. Cuprammonium Complexes and the Structure of Polysaccharides 116 VI. Cuprammonium Complexes and the Shape of Pyranoside Rings 122 VII. Appendices 131 The Chemistry of Ribose BY ROGER W. JEANLOZ, Worcester Foundation for Experimental Biology, Shrewsbury, Massachusetts AND HEWITT G. FLETCHER, JR., National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Public Health Service, Federal Security Agency, Bethesda, Maryland I. Introduction 135 II. Ribose 136 III. Ribose Derivatives 146 The 2-(Aldo-polyhydroxyalkyl)benzimidazoles BY NELSON K. RICHTMYER, National Institute of Arthritis and Metabolic Diseases, National Institutes of Health, Public Health Service, Federal Security Agency, Bethesda, Maryland I. Introduction 175 II. Quinoxalines and Benzimidazoles from Aldoses 176 III. Benzimidazoles from Aldonic Acids 180 IV. Tables 198 Trends in the Development of Granular Adsorbents for Sugar Refining BY ELLIOTT P. BARRETT, Baugh and Sons Company, Philadelphia, Pennsylvania I. Introduction 205 II. Factors Affecting the Depurative Powers of Adsorbents 205 III. Adjustment of Adsorbent Properties to Adsorbent Functions 214 Ascorbic Acid, a By-product in the Manufacture of Sugar BY ROBERT ELLSWORTH MILLER AND SIDNEY M. CANTOR, Research and Development Division, American Sugar Refining Company, Philadelphia, Pennsylvania I. Introduction 231 II. Physical Properties of Aconitic Acid 231 III. Analytical Estimation of Aconitic Acid 234 IV. The Recovery of Aconitic Acid 236 V. Chemistry and Uses of Aconitic Acid in the Manufacture of Sugar 239 244 Friedel-Crafts and Grignard Processes in the Carbohydrate Series BY WILLIAM A. BONNER, Department of Chemistry, Stanford University, California I. Introduction 251 II. Processes Catalyzed by Aluminum Chloride 252 III. Applications of the Grignard Reaction 261 IV. Additional Applications to the Configuration of α-D-Glycopyranosylbenzene 282 V. Physical Properties of Products from Friedel-Crafts and Grignard Reactions 284 The Nitromethane and 2-Nitroethanol Syntheses BY JOHN C. SOWDEN, Washington University, Saint Louis, Missouri I. Introduction 291 II. Some Reactions of Nitroparaffins 203 III. Entry into the Carbohydrate Series with Nitromethane and Aldose Sugars 297 IV. Carbohydrate C-Nitroalcohols 209 V. C-Nitroalcohol Epimers and C-Nitrodeoxy Inositols 310 VI. The Acetylated Carbohydrate C-Nitrooleins 313 VII. The 2-Nitroethanol Synthesis of Higher-Carbon Ketoses 316 ERRATA 319 CUMULATIVE SUBJECT INDEX FOR VOLUMES 1-5 321 409 AUTHOR INDEX FOR VOLUME 6 409 SUBJECT INDEX FOR VOLUME 6 422