Contributors to Volume VI
Preface
Outline of Volumes I-V
Errata and Additions—Volumes I-V
Section I. Separation and Analysis
Chromatography
1. Gas-Liquid Chromatography of Trimethylsilyl Derivatives
2. Gas Chromatographie Estimation of Carbohydrates in Glycosphingolipids
3. Gas-Liquid Chromatography of Trimethylsilyl Ethers of Cyclitols
4. Gas-Liquid Chromatography of Alditol Acetates
5. Gas-Liquid Chromatography of Methylated Sugars
6. Qualitative Thin-Layer Chromatography
7. Quantitative Thin-Layer Chromatography
8. Preparative Thin-Layer Chromatography
9. Partition Chromatography on Ion-Exchange Resins
Chemical, Physical, and Biochemical Methods
10. Determination of Carbonyl Groups with Sodium Cyanide
11. Determination of Carbonyl Groups in Oxidized Cellulose
12. Direct Spectrophotometric Determination of Iodate Following Periodate Oxidation of α-Glycol Groups
13. Determination of Formic Acid in the Periodate Oxidation of Carbohydrates
14. Determination of Starch with Glucoamylase
15. Use of Concanavalin A for Structural Studies
Section II. Preparation of Mono- and Polysaccharides and their Derivatives
Monosaccharides
16. β-D-Allose
17. D-Gulose
18. Aldohexofuranoses
19. Migration of Epoxide Rings and Stereoselective Ring Opening of Acetoxyepoxides
20. Acetoxonium Ion Rearrangements
21. Application of the Wittig Reaction to the Synthesis of Higher Sugars
Polysaccharides
22. Isolation of Polysaccharides from Gram-Negative Bacteria
23. Lipopolysaccharides
24. Teichoic Acids
Deoxy Sugars
25. 5-Deoxy-D-xylo-Hexose
26. 6-Deoxy-D-Glucose (D-Quinovose)
Deoxyhalo Sugars
27. Bromodeoxy Sugars from Epoxides
28. Methyl 4-O-Benzoyl-6-Bromo-6-Deoxyhexopyranosides
29. Chlorodeoxy Sugars via (Chloromethylene)-Dimethyliminium Chloride Reactions
30. 6-Chloro-6-Deoxy-α-D-Glucose
31. Deoxyfluoro Sugars via Displacement of Sulfonyloxy Groups with Tetrabutylammonium Fluoride
32. Deoxyfluoro Sugars from Epoxides
33. Substitution of Hydroxyl Groups with Iodine
Aminodeoxy Sugars
34. Regeneration of Amino Functions from Acetamidodeoxy Sugars
35. Displacement of the p-Tolylsulfonyloxy Group in 1,2:5,6-Di-O-Isopropylidene-3-0-p-Tolylsulfonyl-α-D-Glucofuranose
36. Amino Sugars via Reduction of Azides
37. Synthesis of Amino Sugars with Retention
38. Amino Sugars via Displacement of Sulfonyloxy Groups with Hydrazine
39. Synthesis of Amino Sugars via Oximes
40. Amino Sugars via Anhydro Ring Opening with Ammonia
41. Amino Sugars via Nitroolefins
42. Methyl 3-Deoxy-3-Nitrohexopyranosides
43. Amino Sugars and Amino Cyclitols via Cyclization of Dialdehydes with Nitromethane
44. Synthetic Approaches to cis-Diamino Sugars
45. 2,3-Diamino-2,3-Dideoxy-α-D-Glucose
46. 2,6-Diamino-2,6-Dideoxy-α-D-Galactose
47. 2,6-Diamino-2,6-Dideoxy-β-D-Mannose
48. Preparation of Aminomercapto Furanose Sugars from Dithiocarbamoyl Derivatives
49. 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-α-D-Glucopyranosyl Chloride
Thio Sugars
50. 5-Thio-α-D-Glucopyranose
51. 4-Thio-D-Ribofuranose
Unsaturated Sugars
52. Unsaturated Sugars via Cyclic Thionocarbonates, Cyclic Orthoformates, and Disulfonic Ester Intermediates
53. 2,3-Unsaturated 3-Nitro Glycosides
54. Modified Synthesis of 1-Deoxyald-1-Enopyranose (2-Hydroxyglycal) Esters
Section III. Oxidation
55. Oxidation of Carbohydrates by the Sulfoxide-Carbodiimide and Related Methods
56. Oxidation of Carbohydrates with Dimethyl Sulfoxide-Acetic Anhydride
57. Synthesis of a Ketose from a Partially Benzylated Aldose
58. Oxidation of Carbohydrates with Dimethyl Sulfoxide-Phosphorus Pentaoxide
59. Oxidation with Ruthenium Dioxide and Hypochlorite
60. Selective Catalytic Oxidations of Carbohydrates
61. Unsaturated Glycopyranosiduloses
62. Oxidation of Polysaccharides with Lead Tetraacetate in Dimethyl Sulfoxide
Section IV. Acyclic Sugars
63. 1,1-Bis(acylamido)-1-Deoxyalditols
Section V. Etherification
64. Methylation of Carbohydrates with Methylsulfinyl Anion and Methyl Iodide in Dimethyl Sulfoxide
65. Methylation with Diazomethane-Boron Trifluoride Etherate
66. Benzyl Ethers: Formation and Removal
67. 2,3,4,6-Tetra-O-Benzyl-α-D-glucopyranose
68. Alkylation of Monosaccharides Using Sodium Hydride
69. C-4 Substitution of Methyl D-Glucosides and Malto-Oligosaccharides
70. O-Carboxymethylpachyman
Section VI. Esterification
Phosphate Esters
71. Glycosyl Phosphates
72. L-glycero-Tetrulose (L-Erythrulose) 1-Phosphate
73. D-altro-Heptulose (D-Sedoheptulose) 7-Phosphate
74. 1L-myo-Inositol 1-Phosphate
75. Phosphorylation of Starch and Cellulose with an Amine Salt of Tetrapolyphosphoric Acid
Other Esters
76. 1,2,3,4-Tetra-O-acetyl-β-D-Glucopyranose and Methyl 2,3,4-Tri-0-acetyl-β-D-Glucopyranoside
77. Use of Xanthates in Synthetic Carbohydrate Chemistry
78. Applications of Phenylboronic Acid in Carbohydrate Chemistry
79. Sulfation of Polysaccharides
Section VII. Nucleosides and Nucleotides
80. Isolation of Sugar Nucleotides
81. Pyrimidine Nucleosides by the Trimethylsilyl Method
82. Purine Nucleosides by the Trimethylsilyl Method
83. The Hilbert-Johnson Synthesis of Pyrimidine Nucleosides
84. Selective Phosphorylation of Ribonucleosides
Section VIII. Glycosides
85. Cerebrosides, Isolation
86. Gangliosides, Isolation
87. Use of Mercuric Cyanide and Mercuric Bromide in the Koenigs-Knorr Reaction
88. Synthesis of Oligosaccharides by the Orthoester Method
89. cis-1,2-Glycosides
Section IX. Radioactively Labeled Sugars
90. Preparation of Tritiated Sugars
91. Degradation and Counting of Tritium-Containing Sugars
Section X. Physical Methods
92. Determination of Molecular Weights Osmometry
93. Conformational Analysis via Nuclear Magnetic Resonance Spectroscopy
94. Mass Spectrometry of Carbohydrates
Glossary
Author Index
Subject Index