Protecting groups: Effects on reactivity, glycosylation stereoselectivity, and coupling efficiency

Carbohydrates in Chemistry and Biology

Volumn 1-4, Issue , 2008, Pages 427-447

  Green, Luke G ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b NONE

Author keywords

Carbohydrate; Circumstantial; Glycosylations; Intermediate; Oligosaccharide

Indexed keywords

OLIGOSACCHARIDES;

CIRCUMSTANTIAL; COUPLING EFFICIENCY; GLYCOSYLATIONS; INTERMEDIATE; PROTECTING GROUP;

CARBOHYDRATES;

EID: 84956473833     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527618255.ch17     Document Type: Chapter

References (98)

1. P. J. Kocienski Protecting Groups; Georg Thieme Verlag: Stuttgart: 1994.
2. T. W. Greene, P. G. M. Wuts Protective Groups in Organic Synthesis, Wiley: New York: 1991.
3. M. Bols Carbohydrate Building Blocks, Wiley: New York: 199.
4. S. Hanessian Preparative Carbohydrate Chemistry, Marcel-Dekker: New York: 199.
5. G.-J. Boons Carbohydrate Chemistry, Blackie Academic & Professional: London: 1998.
6. B. Capon Chem. Rev. 1969, 69, 407.
7. M. L. Sinott, W. P. J. Jencks J. Am. Chem. Soc. 1980, 102, 2056.
8. T. L. Amyes, W. P. J. Jencks J. Am. Chem. Soc. 1989, 111, 788.
9. M. L. Sinott Chem. Rev. 1990, 90, 1171.
10. R. Lemieux, K. B. Hendriks, R. V. Stick, K. James J. Am. Chem. Soc. 1975, 97, 4056.
11. A. J. Rhind-Tutt, C. A. Vernon J. Chem. Soc. 1960, 4637.
12. T. Ishikawa, H. G. Fletcher J. Org. Chem. 1969, 34, 563.
13. R. U. Lemieux, G. Huber Can. J. Chem. 1955, 33, 128.
14. P. Delongchamps, C. Moreau, D. FrCchet, P. Atlani Can. J. Chem. 1972, 50, 340.
15. P. Deslongchamps ACS Symposium series: The Anomeric Effect and Associated Stereoelectronic effects; G. R. J. Thatcher Ed.; American Chemical Society: Washington, D. C., 1993; Vol. 549.
16. A. J. Ratcliffe, D. R. Mootoo, C. Webster Andrews, B. Fraser-Reid J. Am. Chem. Soc. 1989, 111, 766.
17. P. Deslongchamps, P. G. Jones, S. Li, A. J. Kirby, S. Kusela, Y. Ma J. Chem. Soc., Perkin Trans. I 1997, 12, 2621.
18. D. Y. Curtin Rec. Chem. Proc., 1954, 15, 111.
19. R. R. Schmidt, J. Michel Angew. Chem. Int. Ed. Engl. 1980, 19, 731.
20. R. R. Schmidt, M. Strumpp Liebig Ann. Chem. 1984, 680.
21. V. Marousek, T. H. Lucas, P. E. Wheat, C. Schuerch Carbohydr. Res. 1978, 60, 85.
22. K. Igarashi, T. Honma, J. Irisawa Carbohydr. Res. 1970, 15, 329.
23. D. Crich, S. X. Sun Tetrahedron 1998, 54, 8321.
24. C. N. Riiber, N. A. Sørensen Kgl. Norske. Videnskab. Selskabs Skrifter 1938, 1, 1.
25. W. G. Overend, C. W. Rees, J. S. Sequeria J. Chem. Soc. 1962, 3429.
26. G. N. Richards Chem. Ind. 1955, 228.
27. M. S. Feather, J. F. Harris J. Org. Chem., 1965, 30, 153.
28. E. A. Kabat, H. Baer, A. E. Bezer, V. Knaub J. Exp. Med., 1948, 88, 43.
29. J. T. Edward Chem. Ind. 1955, 1102.
30. B. Fraser-Reid, A. Wu, C. Webster Andrew, E. Skowronski J. Am. Chem. Soc. 1991, 113, 1434.
31. C. P. J. Glaudemans, H. G. Fletcher J. Am. Chem. Soc. 1965, 87, 4636.
32. N. L. Douglas, S. V. Ley, U. Lücking, S. L. Warriner J. Chem. Soc., Perkin Trans. 1, 1998, 51.
33. L. R. Schroeder, J. W. Green, D. C. Johnson J. Chem. Soc. B, 1966, 447.
34. S. V. Ley, H. W. M. Priepke, S. L. Warriner Angew. Chem. Int. Ed. Engl. 1994, 33, 229.
35. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke, S. L. Warriner, J. Chem. Soc. Perkin Trans. 1, 1997, 351.
36. A plausible explanation for the increased importance of the C4 relative to the C3 based upon hyperconjugation with the endocyclic oxygen lone-pairs has been put forward-C. A. A. van Boeckel, T. Beeta, S. F. van Aelst Tetrahedron, 1984, 40, 4097.
37. Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong J. Am. Chem. Soc. 1999, 121, 734.
38. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke, S. L. Warriner Synlett, 1996, 79.
39. U. Berens, D. Leckel, S. C. Oepen J. Org. Chem. 1995, 60, 820.
40. J.-L. Montchamp, F. Tian, M. E. Hart, J. W. Frost J. Org. Chem. 1996, 61, 3897.
41. That the C4 of galactose has a particular bearing has been noted by other.
42. M. Miljkovic, D. Yeagley, P. Deslongchamps, Y. L. Dory J. Org. Chem. 1997, 62, 759.
43. O. Kwon, S. J. Danishefsky J. Am. Chem. Soc. 1998, 120, 1588.
44. R. U. Lemieux Adv. Carbohydr. Chem. 1954, 9, 1.
45. Although participation from other positions has been postulated by many early investigators, there is little evidence to substantiate that this is possible.
46. R. U. Lemieux, C. Brice, G. Huber Can. J. Chem. 1955, 33, 134.
47. In truth this is a simplification; although attack at C1 of 6 leads to the thermodynamic product, kinetic attack occurs first at the carbonyl carbon leading to an orthoester product. If the reaction is performed under acidic conditions, the acid sensitive orthoester rearranges to form the trans glycoside. However if the donor is very deactivated the orthoester may require a higher acid concentration to induce rearrangement which can result in transesterification (to the acceptor alcohol) predominating, especially if an acetate is used. Destabilizing the orthoester by activating the donor or using benzoyl or pivaloyl protecting groups can resolve this problem.
48. This problem has been reported by many other author.
49. S. Oscarsson Topics in Current Chemistry: Glycoscience; H. Driguuez, J. Thiem Ed.; Springer: Berlin Heidelberg, 1997; Vol. 18.
50. A. V. Nikolaev, T. J. Rutherford, M. A. Ferguson, J. S. Brimacornbe Bioorg. Med. Chem. Lett. 1994, 4, 78.
51. T. Ziegler, B. Adams, P. Kovac, C. P. J. Glaudemans Carbohydr. Chem. 1990, 9, 13.
52. H. Jiao, O. Hindsgaul Angew. Chem. Int. Ed. Engl. 1999, 38, 34.
53. N. Kochetkov The Synthesis of Polysaccharides in The Total Synthesis of Natural Products; J. ApSimon Ed.; Wiley-Interscience: New York, 1992; Vol. 8, p 245.
54. D. Depré, A. Duffels, L. G. Green, R. Lenz, S. V. Ley, C.-H. Wong Chem. Eur. J. 1999, 5, 3326.
55. J. Arnop, M. Haraldsson, J. Lönngren J. Chem. Soc., Perkin Trans. 1 1982, 1841.
56. J. M. Frechékt, C. Schuerch J. Am. Chem. Soc. 1972, 94, 604.
57. J. M. Frechkt, C. Schuerch Polymer Supported Reactions in Organic Synthesis; P. Hodge Ed.; Wiley: Chichester, 1980.
58. Schroeder et al. demonstrated that α-selectivity increased with increasing size of the alcohol L. R. Schroeder, J. W. Green, D. C. Johnson J. Chem. Soc. B 1966, 447.
59. J. E. Wallace, L. R. Schroeder J. Chem. Soc., Perkin Trans. 1 1976, 1938.
60. D. K. Baeschlin, A. R. Chaperon, V. Charbonneau, L. G. Green, S. V. Ley, U. Lücking, E. Walter Angew. Chem. Int. Ed. Engl. 1998, 37, 342.
61. A. S. Campbell, B. Fraser-Reid J. Am. Chem. Soc. 1995, 117, 1038.
62. T. G. Mayer, B. Krazer, R. R. Schmidt Angew. Chem. Int. Ed. Engl. 1994, 33, 217.
63. C. Murakata, T. Ogawa Curbohydr. Res. 1992, 235, 95.
64. The ▵2 effect-R. E. Reeves Adv. Carbohydr. Chem. 1960, 15, 11 the axial oxygen at C2 serves to both to reinforce the anomeric effect, further lowering the ground state energy of the α-leaving group relative to the β-leaving group and sterically shields the β-face thus promoting α-glycosidation.
65. W. S. Kim, S. Hosono, H. Sasai, M. Shibisaki Heterocycles 1996, 42, 795 perchlorate counter-ions have been proposed to provide higher α-selectivities than triflates owing to their slightly reduced fugacity and ether type solvents at room temperature also serve to promote α-selectivity (see chapter on solvent effects).
66. M. Djeter, H. M. Flowers Carbohydr. Res. 1972, 23, 4.
67. V. Behar, S. J. Danishefsky, Angew. Chem. Int. Ed. Engl. 1994, 33, 146.
68. R. Windmuller, R. R. Schmidt, Tetrahedron Lett. 1994, 65, 792.
69. T. Kiyoi, Y. Nakai, H. Kondo, H. Ishida, M. Kiso, A. Hasegawa, Bioorg. Med. Chem. 1996, 4, 1167.
70. J. E. Wallace, L. R. Schroeder J. Chem. Soc., Perkin Trans. I 1976, 1633.
71. R. Eby, C. Schuerch Carbohydr. Res. 1974, 34, 79.
72. P. Sinay Pure Appl. Chem. 1978, 50, 1437.
73. Boons and Zhu have exploited this effect for the synthesis of small oligosaccharides-G.-J. Boons, T. Zhu Synlett 1997, 809.
74. V. Pozsgay Carbohydrates: Synthetic Methods and Applications in Medicinal Chemistry: Synthesis of Oligosaccharides Related to Plant, Vertebrate, and Bacterial Cell-wall Glycans: H. Ogura, A. Hasegawa, T. Suami Ed.; Kodansha, VCH: Tokyo, New York, 1992, p 18.
75. H. Paulsen, W. Rauwald, U. Weichert Liebig. Ann. Chem. 1988, 7.
76. K. Jaarsveld Zegelaar, S. A. W. Smits, G. A. van der Marcel, J. H. van Boom Bioorg. Med. Chem. 1996, 4, 1819.
77. e.g. for sulfoxides D. Kahne, S. Raghavan J. Am. Chem. Soc. 1993, 114, 1580.
78. For glycosyl bromides under halide catalysis this is the rate determining step [6].
79. N. M. Spijker, C. A. Boeckel Angew. Chem. Int. Ed. Engl. 1991, 30, 180.
80. D. Crich, S. X. Sun J. Org. Chem. 1997, 62, 1198.
81. inter alia.
82. M. Wakao, Y. Nakai, K. Fukase, S. Kusumoto Chem. Lett. 1999, 2.
83. R. Rodebaugh, S. Joshi, B. Fraser-Reid, H. M. Geysen J. Org. Chem. 1997, 62, 5660.
84. X.-X. Zhu, M.-S. Cai, R.-L. Zhou Carbohydr. Res. 1997, 303, 261.
85. Y.-M. Zhang, A. Brodzky, P. Sinaÿ, G. Saint-Marcroux, B. Perly Tetrahedron: Asymmetry 1995, 6, 119.
86. V. Pozsgay, E. P. Dubois, L. J. Pannell J. Org. Chem. 1997, 62, 2832.
87. K. Toshima, K. Tatsuta Chem. Rev. 1993, 93, 1503.
88. R. R. Schmidt, Angew. Chem. Int. Ed. Engl. 1986, 25, 212.
89. M. E. Behendt, R. R. Schmidt Tetrahedron Lett. 1993, 34, 10733.
90. T. Iimori, T. Shibizaki, S. Ikegami Tetrahedron Lett. 1996, 37, 2267.
91. G. Scheffler, R. R. Schmidt Tetrahedron Lett. 1997, 38, 2943.
92. G. Scheffler, R. R. Schmidt J. Org. Chem. 1999, 64, 1319.
93. A. G. M. Barrett, B. C. B. Bezuidenhoudt, A. F. Gasiecki, A. R. Howell, M. A. Russell J. Am. Chem. Soc. 1989, 111, 1392.
94. H. Ohtake, T. Iimori, S. Ikegami Tetrahedron Lett. 1997, 38, 3413.
95. H. Waldmann, U. Schmid Chem. Eur. J. 1998, 3, 494.
96. C. Schuerch Acc. Chem. Res. 1973, 6, 184.
97. H. Paulsen Angew. Chem. Int. Ed. Engl. 1982, 21, 155.
98. F. Baressi, O. Hindsgaul Modern Synthetic Methods: Glycosylation Methods in Oligosaccharide Synthesis, B. Ernst, C. Leuman, Ed.; VCH, Basel, 1995.