Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological applications, as conformational probes, or for biological studies. C-Furanosides: Synthesis and Stereochemistry provides a much-needed overview of synthetic and stereochemical principles for C-furanosides: analogs of a 5-membered ring carbohydrate glycoside (furanoside), in which the anomeric oxygen has been replaced with a carbon.
While our understanding of conformational behavior and of stereoselective synthesis in 6-membered ring compounds is quite good, our ability to predict the conformation of 5-membered ring compounds, or to predict the stereochemical outcome of a given reaction, remains anecdotal. Through a comprehensive review of literature approaches to the different C-furanoside stereoisomers, as well as an interpretation of the outcome in terms of a reasonable number of stereochemical models, C-Furanosides: Synthesis and Stereochemistry enables the reader to determine the best approach to a particular C-glycoside compound, and also hopes to provide a certain level of rationalization and predictability for the synthesis of new systems.
1. Chapter A. Introduction - p. 3 2. Chapter A.1. galacto-C-Furanosides (I, β-C-Lyxose) - p. 11 3. Disconnections - p. 12 4. Natural Occurrence - p. 15 5. A.1.1 Disconnection A - p. 16 6. A.1.2 Disconnection B - p. 20 7. A.1.3 Disconnection C - p. 28 8. A.1.4 Disconnection D - p. 43 9. A.1.5 Miscellaneous - p. 46 10. A.1.6 Conclusion - p. 49 11. Chapter A.2. d- and l-altro-C-furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose) - p. 65 12. Disconnections - p. 66 13. Natural Occurrence - p. 69 14. A.2.1 Disconnection A - p. 70 15. A.2.2 Disconnection B - p. 95 16. A.2.3 Disconnection C - p. 100 17. A.2.4 Disconnection D - p. 145 18. A.2.5 Disconnection E - p. 146 19. A.2.6 Miscellaneous - p. 146 20. A.2.7 Conclusion - p. 147 21. Chapter A.3. allo-C-Furanosides (VI, β-C-Ribose) - p. 165 22. Disconnections - p. 166 23. Natural Occurrence - p. 169 24. A.3.1 Disconnection A - p. 170 25. A.3.2 Disconnection B - p. 202 26. A.3.3 Disconnection C - p. 214 27. A.3.4 Disconnection D - p. 247 28. A.3.5 Disconnection E - p. 249 29. A.3.6 Miscellaneous - p. 257 30. A.3.7 Conclusion - p. 259 31. Chapter A.4. Lyxose and Ribose C-Glycosides: Other Results and Further Insight Into Stereochemistry - p. 291 32. A.4.1 Disconnection A - p. 293 33. A.4.2 Disconnection B - p. 323 34. A.4.3 Disconnection C - p. 332 35. A.4.4 Disconnection D - p. 367 36. A.4.5 Miscellaneous - p. 368 37. A.4.6 Conclusion - p. 369 38. Part B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations - p. 381 39. Chapter B. Introduction - p. 385 40. Chapter B.1. Gluco-C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose) - p. 395 41. Disconnections - p. 396 42. Natural Occurrence - p. 399 43. B.1.1 Disconnection A - p. 400 44. B.1.2 Disconnection B - p. 416 45. B.1.3 Disconnection C - p. 423 46. B.1.4 Disconnection D - p. 472 47. B.1.5 Miscellaneous - p. 478 48. B.1.6 Conclusion - p. 480 49. Chapter B.2. ido-C-Furanosides (V/ent-V, α-C-Xylose) - p. 499 50. Disconnections - p. 500 51. Natural Occurrences - p. 504 52. B.2.1 Disconnection A - p. 505 53. B.2.2 Disconnection B - p. 511 54. B.2.3 Disconnection C - p. 513 55. B.2.4 Disconnection D - p. 548 56. B.2.5 Miscellaneous - p. 549 57. B.2.6 Conclusion - p. 550 58. Chapter B.3. manno-C-Furanosides (VII/ent-VII, α-C-Arabinose) - p. 561 59. Disconnections - p. 561 60. Natural Occurrence - p. 565 61. B.3.1 Disconnection A - p. 566 62. B.3.2 Disconnection B - p. 571 63. B.3.3 Disconnection C - p. 576 64. B.3.4 Disconnection D - p. 602 65. B.3.5 Conclusion - p. 602 66. Chapter B.4. Arabinose and Xylose C-Furanosides: Other Results and Further Insight Into Stereochemistry - p. 613 67. Part C. Applications of C-Furanosides - p. 666 68. Introduction - p. 667 69. C.1 Preparation of C-Furanosides - p. 668 70. C.2 Agro-Industry and Farming - p. 669 71. C.3 Ligands for Asymmetric Catalysis - p. 673 72. C.4 Perfumes, Aromas, and Cosmetics - p. 673 73. C.5 Imaging and Diagnostics - p. 674 74. C.6 Pharmaceutical Industry - p. 675 75. C.7 Polymers - p. 701 76. Part D. 1H NMR Vicinal Coupling Constants of C-Furanosides - p. 721 77. Introduction - p. 723 78. Index - p. 747
Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological applications, as conformational probes, or for biological studies. C-Furanosides: Synthesis and Stereochemistry provides a much-needed overview of synthetic and stereochemical principles for C-furanosides: analogs of a 5-membered ring carbohydrate glycoside (furanoside), in which the anomeric oxygen has been replaced with a carbon.
While our understanding of conformational behavior and of stereoselective synthesis in 6-membered ring compounds is quite good, our ability to predict the conformation of 5-membered ring compounds, or to predict the stereochemical outcome of a given reaction, remains anecdotal. Through a comprehensive review of literature approaches to the different C-furanoside stereoisomers, as well as an interpretation of the outcome in terms of a reasonable number of stereochemical models, C-Furanosides: Synthesis and Stereochemistry enables the reader to determine the best approach to a particular C-glycoside compound, and also hopes to provide a certain level of rationalization and predictability for the synthesis of new systems.
1. Chapter A. Introduction - p. 3 2. Chapter A.1. galacto-C-Furanosides (I, β-C-Lyxose) - p. 11 3. Disconnections - p. 12 4. Natural Occurrence - p. 15 5. A.1.1 Disconnection A - p. 16 6. A.1.2 Disconnection B - p. 20 7. A.1.3 Disconnection C - p. 28 8. A.1.4 Disconnection D - p. 43 9. A.1.5 Miscellaneous - p. 46 10. A.1.6 Conclusion - p. 49 11. Chapter A.2. d- and l-altro-C-furanosides (II/ent-II, α-C-Lyxose, α-C-Ribose) - p. 65 12. Disconnections - p. 66 13. Natural Occurrence - p. 69 14. A.2.1 Disconnection A - p. 70 15. A.2.2 Disconnection B - p. 95 16. A.2.3 Disconnection C - p. 100 17. A.2.4 Disconnection D - p. 145 18. A.2.5 Disconnection E - p. 146 19. A.2.6 Miscellaneous - p. 146 20. A.2.7 Conclusion - p. 147 21. Chapter A.3. allo-C-Furanosides (VI, β-C-Ribose) - p. 165 22. Disconnections - p. 166 23. Natural Occurrence - p. 169 24. A.3.1 Disconnection A - p. 170 25. A.3.2 Disconnection B - p. 202 26. A.3.3 Disconnection C - p. 214 27. A.3.4 Disconnection D - p. 247 28. A.3.5 Disconnection E - p. 249 29. A.3.6 Miscellaneous - p. 257 30. A.3.7 Conclusion - p. 259 31. Chapter A.4. Lyxose and Ribose C-Glycosides: Other Results and Further Insight Into Stereochemistry - p. 291 32. A.4.1 Disconnection A - p. 293 33. A.4.2 Disconnection B - p. 323 34. A.4.3 Disconnection C - p. 332 35. A.4.4 Disconnection D - p. 367 36. A.4.5 Miscellaneous - p. 368 37. A.4.6 Conclusion - p. 369 38. Part B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations - p. 381 39. Chapter B. Introduction - p. 385 40. Chapter B.1. Gluco-C-Furanosides (III/ent-III, β-C-Arabinose, β-C-Xylose) - p. 395 41. Disconnections - p. 396 42. Natural Occurrence - p. 399 43. B.1.1 Disconnection A - p. 400 44. B.1.2 Disconnection B - p. 416 45. B.1.3 Disconnection C - p. 423 46. B.1.4 Disconnection D - p. 472 47. B.1.5 Miscellaneous - p. 478 48. B.1.6 Conclusion - p. 480 49. Chapter B.2. ido-C-Furanosides (V/ent-V, α-C-Xylose) - p. 499 50. Disconnections - p. 500 51. Natural Occurrences - p. 504 52. B.2.1 Disconnection A - p. 505 53. B.2.2 Disconnection B - p. 511 54. B.2.3 Disconnection C - p. 513 55. B.2.4 Disconnection D - p. 548 56. B.2.5 Miscellaneous - p. 549 57. B.2.6 Conclusion - p. 550 58. Chapter B.3. manno-C-Furanosides (VII/ent-VII, α-C-Arabinose) - p. 561 59. Disconnections - p. 561 60. Natural Occurrence - p. 565 61. B.3.1 Disconnection A - p. 566 62. B.3.2 Disconnection B - p. 571 63. B.3.3 Disconnection C - p. 576 64. B.3.4 Disconnection D - p. 602 65. B.3.5 Conclusion - p. 602 66. Chapter B.4. Arabinose and Xylose C-Furanosides: Other Results and Further Insight Into Stereochemistry - p. 613 67. Part C. Applications of C-Furanosides - p. 666 68. Introduction - p. 667 69. C.1 Preparation of C-Furanosides - p. 668 70. C.2 Agro-Industry and Farming - p. 669 71. C.3 Ligands for Asymmetric Catalysis - p. 673 72. C.4 Perfumes, Aromas, and Cosmetics - p. 673 73. C.5 Imaging and Diagnostics - p. 674 74. C.6 Pharmaceutical Industry - p. 675 75. C.7 Polymers - p. 701 76. Part D. 1H NMR Vicinal Coupling Constants of C-Furanosides - p. 721 77. Introduction - p. 723 78. Index - p. 747
