Benzylidene acetal fragmentation route to 6-deoxy sugars: Direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of β-D-rhamnosides from D-mannosyl glycosyl donors

Journal of the American Chemical Society

Volumn 126, Issue 26, 2004, Pages 8232-8236

  Crich, David ^a   Yao, Qingjia ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; STEREOCHEMISTRY; SUGARS; SYNTHESIS (CHEMICAL);

GLYCOSYLATION; RADICAL FRAGMENTATION;

AROMATIC COMPOUNDS;

BACTERIUM LIPOPOLYSACCHARIDE; BENZYLIDENEACETONE; DEOXYSUGAR; GALACTOSE; GLUCOSE DERIVATIVE; MANNOSE; RHAMNOSE;

ARTICLE; CARBOXYLATION; CHEMICAL MODIFICATION; ESCHERICHIA COLI; FRAGMENTATION REACTION; GLYCOSYLATION; PRODUCTIVITY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

BENZYLIDENE COMPOUNDS; ESCHERICHIA; GLYCOSYLATION; LIPOPOLYSACCHARIDES; MANNOSIDES; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; RHAMNOSE;

EID: 3042758507     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048070j     Document Type: Article

References (98)

1. (a) Jennings, H. J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155-208.
2. (b) Fedson, D. S.; Shapiro, E. D.; Laforce, F. M.; Mufson, M. A.; Spika, J. S.; Breiman, R. F.; Broome, C. V.; Musher, D. M. Arch. Intern. Med. 1994, 154, 2531-2535.
3. (c) Goldblatt, D. J. Med. Microbiol. 1998, 47, 563-567.
4. (d) Djuretic, T.; Ryan, M. J.; Millar, E.; Fairley, C. K.; Goldblatt, D. J. Infection 1998, 37, 54-58.
5. (a) Hirooka, M.; Yoshimura, A.; Saito, I.; Ikawa, F.; Uemoto, Y.; Koto, S.; Takabatake, A.; Taniguchi, A.; Shinoda, Y.; Morinaga, A. Bull. Chem. Soc. Jpn. 2003, 76, 1409-1421.
6. (b) Spitali, M.; Smith, A. R. M. J. Phytopathol. 2000, 148, 563-568.
7. (c) Knirel, Y. A.; Shashkov, A. S.; Senchenkova, S. N.; Ajika, Y.; Fukuoka, S. Carbohydr. Res. 2002, 337, 1589-1591.
8. (d) Cerantola, S.; Montrozier, H. Eur. J. Biochem. 1997, 246, 360-366.
9. (e) Winn, A. M.; Wilkinson, S. Q. Carbohydr. Res. 1996, 294, 109-115.
10. (f) Senchenkova, S. N.; Shashkov, A. S.; Keckes, M. L.; Ahohuendo, B. C.; Knirel, Y. A.; Rudolph, K. Carbohydr. Res. 2000, 329, 831-838.
11. (g) Vinogradov, E. V.; Shashkov, A. S.; Knirel, Y. A. Carbohydr. Res. 1991, 212, 307-311.
12. (h) Vinogradov, E. V.; Campos-Portuguez, S.; Yokata, A.; Mayer, H. Carbohydr. Res. 1994, 261, 103-109.
13. (i) Molinaro, A.; Silipo, A.; Lanzetta, R.; Newman, M.-A.; Dow, J. M.; Parrilli, M. Carbohydr. Res. 2003, 338, 277-281.
14. (j) Perry, M. B.; Richards, J. C. Carbohydr. Res. 1990, 205, 371-376.
15. (k) Beynon, L. M.; Bundle, D. R.; Perry, M. B. Can. J. Chem. 1990, 68, 1456-1466.
16. (a) Zorbach, W. W.; Tio, C. O. J. Org. Chem. 1961, 26, 3543-3545.
17. (b) Haskins, W. T.; Hann, R. M.; Hudson, C. S. J. Am. Chem. Soc. 1946, 68, 628-632.
18. (c) Ramm, M.; Lobe, M.; Hamburger, M. Carbohydr. Res. 2003, 338, 109-112.
19. Bundle has previously developed a synthesis of S-ethyl 2-O-acetyl-3,4-di-O-benzyl-β-D-thiorhamnopyranoside from D-mannose as an α-rhamnosyl donor: Kihlberg, J.; Eichler, E.; Bundle, D. R. Carbohydr. Res. 1991, 211, 59-75.
20. Crich, D.; Picione, J. Org. Lett. 2003, 5, 781-784.
21. (a) Barresi, F.; Hindsgaul, O. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996; pp 251-276.
22. (b) Demchenko, A. V. Synlett 2003, 1225-1240.
23. (c) Pozsgay, V.; In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, pp 319-343.
24. (d) Gridley, J. J.; Osborn, H. M. I. J. Chem. Soc., Perkin Trans. 1 2000, 1471-1491.
25. (a) Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 4506-4507.
26. (b) Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217-11223.
27. (c) Crich, D.; Sun, S. Tetrahedron 1998, 54, 8321-8348.
28. (d) Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020.
29. (e) Crich, D.; Smith, M. J. Am. Chem. Soc. 2002, 124, 8867-8869.
30. (f) Crich, D.; Li, H. J. Org. Chem. 2000, 65, 801-805.
31. For developmental work in other laboratories see: (a) Yun, M.; Shin, Y.; Chun, K. H.; Jen, S. Bull. Chem. Soc. Kor. 2000, 21, 562-566.
32. (b) Weingart, R.; Schmidt, R. R. Tetrahedron Lett. 2000, 41, 8753-8758.
33. (c) Tsuda, T.; Sato, S.; Nakamura, S.; Hashimoto, S. Hetereocycles 2003, 59, 509-515.
34. (d) Kim, K. S.; Kim, J. H.; Lee, Y. J.; Lee, Y. J.; Park, J. J. Am. Chem. Soc. 2001, 123, 8477-8481.
35. (e) Litjens, R. E. J. N.; Leeuwenburgh, M. A.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8693-8696.
36. (f) Codée, J. D. C.; van den Bos, L. J.; Litjens, R. E. J. N.; Overkleeft, H. S.; van Boeckel, C. A. A.; van Boom, J. H.; van der Marel, G. A. Tetrahedron 2004, 60, 1057-1064.
37. (g) Durón, S. G.; Polat, T.; Wong, C.-H. Org. Lett. 2004, 6, 839-841.
38. (a) Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2002, 124, 2263-2266.
39. (b) Dudkin, V. Y.; Crich, D. Tetrahedron Lett. 2003, 44, 1787-1789.
40. (c) Dudkin, V. Y.; Miller, J. S.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 1791-1793.
41. (d) Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Jeong, K.-S. Synlett 2003, 1311-1314.
42. (e) Crich, D.; de la Mora, M. A.; Cruz, R. Tetrahedron 2002, 58, 35-44.
43. (f) Crich, D.; Dai, Z. Tetrahedron 1999, 55, 1569-1580.
44. (g) Nicolaou, K. C.; Mitchell, H. J.; Rodriguez, R. M.; Fylaktakidou, K. C.; Suzuki, H.; Conley, S. R. Chem. Eur. J. 2000, 6, 3149-3165.
45. (h) Crich, D.; Li, H.; Yao, Q.; Wink, D. J.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 5826-5828.
46. (i) Crich, D.; Li, H. J. Org. Chem. 2002, 67, 4640-4646.
47. (j) Dudkin, V. K.; Miller, J. S.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 736-738.
48. (k) Mandal, M.; Dudkin, V. Y.; Geng, X.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2004, 43, 2557-2561.
49. (l) Wu, X.; Schmidt, R. R. J. Org. Chem. 2004, 69, 1853-1857.
50. (a) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1035-1044.
51. (b) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1045-1053.
52. (c) Hanessian, S. Org. Synth. 1987, 65, 243-247.
53. (d) Hullar, T. L.; Siskin, S. B. J. Org. Chem. 1970, 35, 225-227.
54. (e) Hanessian, S. Adv. Chem. Ser. 1968, 74, 159-201.
55. (f) Szarek, W. A. Adv. Carbohydr. Chem. Biochem. 1973, 28, 225-306.
56. (g) Paulsen, H. Adv. Carbohydr. Chem. Biochem. 1971, 26, 127-195.
57. (h) Gelas, J. Adv. Carbohydr. Chem. Biochem. 1981, 39, 71-156.
58. (i) Chana, J. S.; Collins, P. M.; Farnia, F.; Peacock, D. J. J. Chem. Soc., Chem. Commun. 1988, 94-96.
59. (j) McNulty, J.; Wilson, J.; Rochon, A. C. J. Org. Chem. 2004, 69, 563-565.
60. The majority of NBS-mediated cleavage of carbohydrate-based benzylidene acetals has been conducted with the residual alcohols either unprotected or protected as esters. Reports occasionally surface on the application of the reaction in the presence of benzyl-type ethers, but yields are generally low and difficult to reproduce: Liotta, L. J.; Dombi, K. L.; Kelley, S. A.; Targontsidis, S.; Morin, A. M. Tetrahedron Lett. 1997, 38, 7833-7834.
61. (a) Roberts, B. P.; Smits, T. M. Tetrahedron Lett. 2001, 42, 3663-3666.
62. (b) Roberts, B. P.; Smits, T. M. Tetrahedron Lett. 2001, 42, 137-140.
63. (c) Dang, H.-S.; Roberts, B. P.; Sekhon, J.; Smits, T. M. Org. Biomol. Chem. 2003, 1, 1330-1341.
64. (d) Fielding, A. J.; Franchi, P.; Roberts, B. P.; Smits, T. M. J. Chem. Soc., Perkin Trans. 2 2002, 155-163.
65. (e) Cai, Y.; Dang, H. S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 2002, 2449-2458.
66. (f) Jeppesen, L. M.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1973, 27, 3579-3585.
67. There are no published reports of this chemistry in the presence of benzyl ethers. Certainly, in our hands, benzyl ether cleavage is competitive with benylidene acetal fragmentation.
68. For a preliminary communication see: Crich, D.; Yao, Q. Org. Lett. 2003, 5, 2189-2191.
69. (a) Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900-5902.
70. (b) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142-3147.
71. (c) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
72. (a) Brunckova, J.; Crich, D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619-6622.
73. (b) Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605-615.
74. Yamazaki, N.; Eichenberger, E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623-6626.
75. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991-2070.
76. Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566-3570.
77. Chan, T. H.; Brook, M. A.; Chaly, T. Synthesis 1983, 203-205.
78. (a) Garegg, P. J.; Janesson, P.-E.; Lindberg, B.; Lindh, F.; Lonngren, J.; Kvarnstrom, I.; Nimmich, W. Carbohydr. Res. 1980, 78, 127-132.
79. (b) Garegg, P. J.; Lindberg, B.; Kvarnstrom, I. Carbohydr. Res. 1979, 77, 171-178.
80. Gennari, C.; Carcano, M.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. J. Org. Chem. 1997, 62, 4746-4755.
81. Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326.
82. Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293-297.
83. (a) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461-1463.
84. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
85. Crich, D.; de la Mora, M.; Vinod, A. U. J. Org. Chem. 2003, 68, 8142-8148.
86. (a) Gaunt, M. J.; Yu, J.; Spencer, J. B. J. Org. Chem. 1998, 63, 4172-4173.
87. (b) Wright, J. A.; Yu, J.; Spencer, J. B. Tetrahedron Lett. 2001, 42, 4033-4036.
88. (c) Xia, J.; Abbas, S. A.; Locke, R. D.; Piskorz, C. F.; Alderfer, J. L. Tetrahedron Lett. 2000, 41, 169-173.
89. (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
90. (b) David, S. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Dekker: New York, 1997; pp 69-83.
91. Crich, D.; Cai, W.; Dai, Z. J. Org. Chem. 2000, 65, 1291-1297.
92. (a) Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
93. (b) Garegg, P. J. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Dekker: New York, 1993; pp 53-67.
94. Codée, J. D. C.; Litjens, R. E. J. N.; den Heeten, R.; Overkleeft, H. S.; van Boom, J. H.; van der Marel, G. A. Org. Lett. 2003, 5, 1519-1522.
95. (a) Garcia, B. A.; Poole, J. L.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597-7598.
96. (b) Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269-4279.
97. Cook, A. F.; Maichuk, D. T. J. Org. Chem. 1970, 35, 1940-1943.
98. Note that it was necessary to remove the chloroacetate group prior to the radical reaction to prevent competitive reduction of the relatively weak chloroacetate C-Cl bond by the stannane.