4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. Improved second-generation acetals for the stereoselective formation of β-D-mannopyranosides and regioselective reductive radical fragmentation to β-D-rhamnopyranosides. Scope and limitations

Journal of Organic Chemistry

Volumn 71, Issue 9, 2006, Pages 3452-3463

  Crich, David ^a   Bowers, Albert A ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHORSULFONIC ACID; STEREOSELECTIVE FORMATION; THIOMANNOSIDE DONORS;

BORON COMPOUNDS; CARBOHYDRATES; MIXTURES; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

ACETAL RESINS;

4,6 O [1 CYANO 2 (2 IODOPHENYL)ETHYLIDENE]ACETAL DERIVATIVE; ACETAL DERIVATIVE; ACETIC ACID DERIVATIVE; BETA DEXTRO MANNOPYRANOSIDE DERIVATIVE; BETA DEXTRO RHAMNOPYRANOSIDE DERIVATIVE; BORON TRIFLUORIDE; CAMPHOR DERIVATIVE; CAMPHORSULFONIC ACID; CARBOHYDRATE; MANNOSIDE; PYRANOSIDE; SULFONIC ACID DERIVATIVE; TIN; TRIETHYL (2 IODOPHENYL)ORTHOACETATE; UNCLASSIFIED DRUG;

ARTICLE; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION TIME; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ACETALS; FREE RADICALS; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; NITRILES; TEMPERATURE;

EID: 33646271159     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0526688     Document Type: Article

References (99)

1. (a) Beynon, L. M.; Bundle, D. R.; Perry, M. B. Can. J. Chem. 1990, 68, 1456-1466.
2. (b) Perry, M. B.: Richards, J. C. Carbohydr. Res. 1990, 205, 371-376.
3. (c) Vinogradov, E. V.; Shashkov, A. S.; Knirel, Y. A. Carbohydr. Res. 1991, 272, 307-311.
4. (d) Vinogradov, E. V.; Campos-Portuguez, S.; Yokota, A.; Mayer, H. Carbohydr. Res. 1994, 261, 103-109.
5. (e) Winn, A. M.; Wilkinson, S. G. Carbohydr. Res. 1996, 294, 109-115.
6. (f) Cerantola, S.; Montrozier, H. Eur. J. Biochem. 1997, 246, 360-366.
7. (g) Senchenkova, S. y. N.; Shashkov, A. S.; Kecskes, M. L.; Ahohuendo, B. C.; Knirel, Y. A.; Rudolph, K. Carbohydr. Res. 2000, 329, 831-838.
8. (h) Spitali, M.; Smith, A. R. W. J. Phytopathol. 2000, 148, 563-568.
9. (i) Knirel, Y. A.; Shashkov, A. S.; Senchenkova, S. Y. N.; Ajiki, Y.; Fukuoka, S. Carbohydr. Res. 2002, 337, 1589-1591.
10. (j) Molinaro, A.; Silipo, A.; Lanzetta, R.; Newman, M.-A.; Dow, J. M.; Parilli, M. Carbohydr. Res. 2003, 338, 277-281.
11. (k) 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.
12. (a) Haskins, W. T.; Hann, R. M.; Hudson, C. S. J. Am. Chem. Soc. 1946, 68, 628-632.
13. (b) Zorbach, W. W.; Tio, C. O. J. Org. Chem. 1961, 26, 3543-3545.
14. (c) Bundle, D. R.; Eichler, E.; Kihlberg, J. Carbohydr. Res. 1991, 211, 59-75.
15. (d) Ramm, M.; Lobe, M.; Hamburger, M. Carbohydr. Res. 2003, 338, 109-112.
16. (a) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1035-1044.
17. (b) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1045-1053.
18. (c) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1053-1058.
19. (d) Chana, J. S.; Collins, P. M.; Farnia, F.; Peacock, D. J. J. Chem. Soc., Chem. Commun. 1988, 2, 94-96.
20. (e) Binkley, R. W.; Goewey, G. S.; Johnston, J. C. J. Org. Chem. 1984, 49, 992-996.
21. (f) Hanessian, S. Org. Synth. 1987, 65, 243-247.
22. (g) Hullar, T. L.; Siskin, S. B. J. Org. Chem. 1970, 35, 225-227.
23. (e) Hanessian, S. Adv. Chem. Ser. 1968, 74, 159-201.
24. (h) Szarek, W. A. Adv. Carbohydr. Chem. Biochem. 1973, 28, 225-306.
25. (i) Paulsen, H. Adv. Carbohydr. Chem. Biochem. 1971, 26, 127-195.
26. (j) Gelas, J. Adv. Carbohydr. Chem. Biochem. 1981, 39, 71-156.
27. (a) Crich, D.; Picione, J. Org. Lett. 2003, 5, 781-784.
28. (b) Crich, D.; Vinod, A. U.; Picione, J. J. Org. Chem. 2003, 68, 8453-8458.
29. (c) Crich, D.; Hutton, T.; Banerjee, A.; Jayalath, P.; Picione, J. Tetrahedron: Asymmetry 2005, 16, 105-119.
30. (a) Bedini, E.; Carabellese, A.; Barone, G.; Parilli, M. J. Org. Chem. 2005, 70, 8064-8070.
31. (b) Bedini, E.; De Castro, C.; Erbs, G.; Manogoni, L.; Dow, J. M.; Newman, M.-A.; Parilli, M.; Unverzagt, C. J. Am. Chem. Soc. 2005, 127, 2414-2416.
32. (a) Crich, D.; Li, H.; Yao, Q.; Wink, D. J.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 121, 5826-5828.
33. (b) Crich, D.; Li, H. J. Org. Chem. 2002, 67, 4640-4646.
34. (c) Crich, D.; Dai, Z. Tetrahedron 1999, 55, 1569-1580.
35. (d) Crich, D.; Barba, G. R. Tetrahedron Lett. 1998, 39, 9339-9342.
36. (e) Crich, D.; de la Mora, M. A.; Cruz, R. Tetrahedron 2002, 58, 35-44.
37. (f) Crich, D.; Banerjee, A.; Yao, Q. J. Am. Chem. Soc. 2004, 126, 14930-14934.
38. (g) Crich, D.; Banerjee, A. Org. Lett. 2005, 7, 1935-1938.
39. (h) Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2002, 124, 2263-2266.
40. (i) Dudkin, V. Y.; Crich, D. Tetrahedron Lett. 2003, 44, 1787-1789.
41. (j) Dudkin, V. K.; Miller, J. S.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 736-738.
42. (k) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431-434.
43. (l) Nicolaou, K. C.; Mitchell, H. J.; Rodriguez, R. M.; Fylaktakidou, K. C.; Suzuki, H.; Conley, S. R. Chem. Eur. J. 2000, 6, 3149-3165.
44. (m) Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Jeong, K.-S. Synlett 2003, 1311-1314.
45. (n) Wu, X.; Schmidt, R. R. J. Org. Chem. 2004, 69, 1853-1857.
46. (o) Kwon, Y. T.; Lee, Y. J.; Lee, K.; Kim, K. S. Org. Lett. 2004, 6, 3901-3904.
47. (p) Tanaka, S.-i.; Takashina, M.; Tokimoto, H.; Fujimoto, Y.; Tanaka, K.; Fukase, K. Synlett 2005, 2325-2328.
48. (a) Roberts, B. P.; Smits, T. M. Tetrahedron Lett. 2001, 42, 3663-3666.
49. (b) Roberts, B. P.; Smits, T. M. Tetrahedron Lett. 2001, 42, 137-140.
50. (c) Dang, H.-S.; Roberts, B. P.; Sekhon, J.; Smits, T. M. Org. Biomol. Chem. 2003, 1, 1330-1341.
51. (d) Fielding, A. J.; Franchi, P.; Roberts, B. P.; Smits, T. M. J. Chem. Soc., Perkin Trans. 2 2002, 155-163.
52. (e) Cai, Y.; Dang, H. S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 2002, 2449-2458.
53. (f) Jeppesen, L. M.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1973, 27, 3579-3585.
54. For a rare exception see: Liotta, L. J.; Dombi, K. L.; Kelley, S. A.; Targontsidis, S.; Morin, A. M. Tetrahedron. Lett. 1997, 38, 7833-7834.
55. Wenger, R. M. Helv. Chim. Acta 1983, 66, 2308-2321.
56. (a) Ingold, K. U.; Malatesta, V. J. Am. Chem. Soc. 1981, 103, 609-614.
57. (b) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615-619.
58. (a) Crich, D.; Yao, Q. Org. Lett. 2003, 5, 2189-2191.
59. (b) Crich, D.; Yao, Q. J. Am. Chem. Soc. 2004, 126, 8232-8236.
60. (a) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565-2575.
61. (b) Rychnovsky, S. D.; Swenson, S. S. Tetrahedron 1997, 53, 16489-16502.
62. (a) Hind, C. R. K.; Collins, P. M.; Renn, D.; Cook, R. B.; Caspi, D.; Baltz, M. L.; Pepys, M. B. J. Exp. Med. 1984, 159, 1058-1069.
63. (b) Liptak, A.; Szabo, L. Carbohydr. Res. 1984, 184, C5-C8.
64. (c) Hashimoto, H.; Hiruma, K.; Tamura, J.-I. Carbohydr. Res. 1988, 177, C9-C12.
65. (d) Collins, P. M.; McKinnon, A. C.; Manro, A. Tetrahedron Lett. 1989, 30, 1399-1400.
66. For a review of methods, see: Ziegler, T. Top. Curr. Chem. 1997, 186, 203-229.
67. 2-promoted method, see: (a) Ziegler, T.; Herold, G. Liebigs. Ann. Chem. 1994, 859-866.
68. (b) Ziegler, T. Tetrahedron Lett. 1994, 35, 6857-6860.
69. (a) Wardrop, D. J.; Velter, A. I.; Forslund, R. E. Org. Lett. 2001, 3, 2261-2264.
70. (b) Wardrop, D. J.; Forslund, R. E.; Landrie, C. L.; Velter, A. I.; Wink, D.; Surve, B. Tetrahedron: Asymmetry 2003, 14, 929-940.
71. Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020.
72. Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326.
73. (a) 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.
74. (b) 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.
75. Curran, D. P.; Seong, C. M. Synlett 1991, 107-108.
76. Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron 1983, 39, 967-973.
77. For a review of ortho ester formation: De Wolfe, R. H. Synthesis 1974, 153-172.
78. (a) Eliel, E.; Nader, F. W. J. Am. Chem. Soc. 1970, 92, 584-589.
79. (b) Eliel, E.; Nader, F. W. J. Am. Chem. Soc. 1970, 92, 3050-3055.
80. (c) Rychnovsky, S. D.; Kim, J. Tetrahedron Lett. 1991, 32, 7223-7224.
81. (d) Cf. ref 16 and references therein.
82. (a) Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3641-3642.
83. (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
84. (c) Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1989, 54, 2492-2494.
85. (d) Giese, B.; Kopping, B. Tetrahedron Lett. 1989, 30, 681-684.
86. Crich, D.; Cai, W. J. Org. Chem. 1999, 64, 4926-4930.
87. Deng, S.; Yu, B.; Guo, Z.; Hui, Y. J. Carbohydr. Chem. 1998, 17, 439-452.
88. Precedent for the formation of similar substances combining two molecules of a glycosyl donor, with migration of a single ester to the anomeric position, can be found in the work of Whitfield and co-workers: Nukada, T.; Berces, A.; Whitfield, D. M. J. Org. Chem. 1999, 64, 9030-9045.
89. However, it did prove possible to selectively cleave a chloroacetate ester in the presence of the first-generation radical precursor with ethylenediamine, cf. ref 11b.
90. Kunesch, N.; Miet, C.; Poisson, J. Tetrahedron Lett. 1987, 28, 3569-3572.
91. Comparison with the Hanessian-Hullar NBS mediated cleavage reveals significant differences between the two reactions in the galactopyranose series, but this is due to the operation of different mechanisms. The work described here, like that of Roberts, is a pure radical fragmentation, whereas the Hanessian-Hullar reaction is a nucleophilic ring opening by the bromide ion: McNulty, J.; Wilson, J.; Rochon, A. C. J. Org. Chem. 2004, 69, 563-565.
92. Precedent exists in the literature for this type of Lewis acid mediated methyl galactopyranoside to methyl galactofuranoside rearrangement. Ziegler, T.; Eckhardt, E.; Herold, G. Liebigs Ann. Chem. 1992, 441-451.
93. 31
94. Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217-11223.
95. Gin, D. Y.; Garcia, B. A. J. Am. Chem. Soc. 2000, 122, 4269-4279.
96. Such intermediates are well-known in DMTST activations. For a recent example, see: Davis, B. G.; Grayson, E. J.; Ward, S. J.; Hall, A. L.; Rendle, P. M.; Gamblin, D. P.; Batsanov, A. S. J. Org. Chem. 2005, 70, 9740-9754.
97. Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112-13119.
98. Jensen, H. H.; Nordstrom, L. U.; Bols, M. J. Am. Chem. Soc. 2004, 126, 9205-9213.
99. Crich, D.; Chandrasekera, S. Angew. Chem., Int. Ed. 2004, 43, 5386-5389.