Chemistry of glucal halohydrins(II): An unusual protecting group effect in the competitive formation of formyl furanosides and methyl glycosides

Carbohydrate Research

Volumn 300, Issue 4, 1997, Pages 301-313

  Kozlowski, John S ^a   Marzabadi, Cecilia H ^a,b   Rath, Nigam P ^a   Spilling, Christopher D ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

C Formyl furanosides; Glycosides; Halohydrins; Iodolactone; Ring contraction

Indexed keywords

FUNCTIONAL GROUP; GLYCOSIDE; METHYLGLUCOSIDE; PROTECTIVE AGENT;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0031001224     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)00054-2     Document Type: Article

References (71)

1. (a) G. Trummlitz and J.G. Moffatt, J. Org. Chem., 38 (1973) 1841-1845;
2. (b) C.R. Bertozzi, P.D. Hoeprich, Jr., and M.D. Bednarski, J. Org Chem., 57 (1992) 6092-6094;
3. (c) C.R. Bertozzi, D.G. Cook, W.R. Kobertz, F. Gonzales-Scarano, and M.D. Bednarski, J. Am Chem. Soc., 114 (1992) 10639;
4. (d) H. Dietrich and R.R. Schmidt, Carbohydr. Res., 250 (1993) 161;
5. (e) S. Hanessian, P.C. Tyler, G. Demailly, and Y. Chapleur, J. Am. Chem. Soc., 103 (1981) 6243-6246;
6. (f) J.G. Buchanan, Prog. Chem. Nat. Prod., 44 (1983) 243.
7. (a) A. Dondoni and M.-C. Scherrmann, J. Org. Chem., 59 (1994) 6404-6412;
8. (b) H. Albrecht, D.B. Repke, and J.G. Moffatt, J. Org. Chem., 38 (1973) 1836-1840;
9. (c) S.A. Babirad, Y. Wang, and Y. Kishi, J. Org. Chem., 52 (1987) 1370-1372;
10. (d) Y. Wang, S.A. Babirad, and Y. Kishi, J. Org. Chem., 57 (1992) 468-481;
11. (e) T. Haneda, P.G. Goekjian, S.H. Kim, and Y. Kishi, J. Org. Chem., 57 (1992) 490-498;
12. (f) W.R. Kobertz, C.R. Bertozzi, and M.D. Bednarski, Tetrahedron Lett., 33 (1992) 737-740;
13. (g) C.R. Bertozzi, and M.D. Bednarski, Tetrahedron Lett., 33 (1992) 3109-3112.
14. H. Redlich, Angew. Chem. Int. Ed. Engl., 33 (1994) 1345-1347.
15. (a) G. Ledderhose, Z. Physiol. Chem., 4 (1880) 139;
16. (b) B.C. Bera, A.B. Foster, and M. Stacey, J. Chem. Soc., (1956) 4531-4535;
17. (c) D. Horton and K.D. Philips, Carbohydr. Res., 30 (1973) 367-374;
18. (d) A.B. Foster, Chem. Ind., (1955) 627;
19. (e) J. Defaye, Adv. Carbohydr. Chem. Biochem., 25 (1970) 181-228;
20. (f) J. Defaye, Bull. Soc. Chim. Fr., 1964, 999-1002;
21. (g) P.A. Levene, J. Biol. Chem., 39 (1919) 69-76;
22. (h) ibid., 59 (1924) 135-139.
23. For some examples see: (a) J.M. Sugihara and D.L. Schmidt, J. Org. Chem., 26 (1961) 4612-4615;
24. (b) P. Brigl and H. Grüner, Chem. Ber., 66 (1933) 1945-1949;
25. (c) R.C. Hockett, M. Zief, and R.M. Goepp, J. Am. Chem. Soc., 68 (1946) 935-937;
26. (d) R.C. Hockett, M. Conley, M. Yusem, and R.I. Mason, J. Am. Chem. Soc., 68 (1946) 922-926;
27. (e) S. Soltzberg, R.M. Goepp, and S. Freudenberg, J. Am. Chem. Soc., 68 (1946) 919-921.
28. (a) A. Kirschning, Liebigs Ann. Chem. (1995) 2053-2056;
29. (b) K.R. Wood and P.W. Kent, J. Chem. Soc. (C) (1967) 2422-2425;
30. (c) A. Kaye, S. Neidle, and C.B. Reese, Tetrahedron Lett. (1988) 29, 1841-1844.
31. (a) R.U. Lemieux and B. Fraser-Reid, Can. J. Chem., 42 (1964) 539-546;
32. (b) R.U. Lemieux and B. Fraser-Reid, Can. J. Chem., 42 (1964) 547-549.
33. G. Arpad, Magy. Kem. Foly., 68 (1962) 211-212.
34. (a) H.H. Baer, F.H. Mateo, and L. Siemsen, Carbohydr. Res., 187 (1989) 67-92;
35. (b) A.B. Charette and B. Côté, J. Org. Chem., 58 (1993) 933-936;
36. (c) A.B. Charette, J. Marcoux, and B. Côté, Tetrahedron Lett., 49 (1991) 7215-7218;
37. (d) G.W.J. Fleet and L.C. Seymour, Tetrahedron Lett., 28 (1987) 3015-3018;
38. (e) F.M. El Sayed Ahamed, S. David, and J.-M. Vatele, Carbohydr. Res., 155 (1986) 19-31;
39. (f) A. Grouiller, H. Bazin, and C. Gagnieu, Tetrahedron Lett., 23 (1982) 2559-2562. For reviews, see: D.H. Bal and F.W. Parrish, Adv. Carbohydr. Chem. Biochem., 24 (1969) 139-197; L. Hough and A.C. Richardson, in W. Pigman and D. Horton (Eds.), The Carbohydrates, 2nd ed., Vol. 1A, Academic Press, New York, 1972, pp 140-146; J.G. Buchanan, in G. O Aspinall (Ed.), Carbohydrates, MTP International Review of Science, Vol. 7, 1973, pp 37-70.
40. (f) A. Grouiller, H. Bazin, and C. Gagnieu, Tetrahedron Lett., 23 (1982) 2559-2562. For reviews, see: D.H. Bal and F.W. Parrish, Adv. Carbohydr. Chem. Biochem., 24 (1969) 139-197; L. Hough and A.C. Richardson, in W. Pigman and D. Horton (Eds.), The Carbohydrates, 2nd ed., Vol. 1A, Academic Press, New York, 1972, pp 140-146; J.G. Buchanan, in G. O Aspinall (Ed.), Carbohydrates, MTP International Review of Science, Vol. 7, 1973, pp 37-70.
41. (f) A. Grouiller, H. Bazin, and C. Gagnieu, Tetrahedron Lett., 23 (1982) 2559-2562. For reviews, see: D.H. Bal and F.W. Parrish, Adv. Carbohydr. Chem. Biochem., 24 (1969) 139-197; L. Hough and A.C. Richardson, in W. Pigman and D. Horton (Eds.), The Carbohydrates, 2nd ed., Vol. 1A, Academic Press, New York, 1972, pp 140-146; J.G. Buchanan, in G. O Aspinall (Ed.), Carbohydrates, MTP International Review of Science, Vol. 7, 1973, pp 37-70.
42. (f) A. Grouiller, H. Bazin, and C. Gagnieu, Tetrahedron Lett., 23 (1982) 2559-2562. For reviews, see: D.H. Bal and F.W. Parrish, Adv. Carbohydr. Chem. Biochem., 24 (1969) 139-197; L. Hough and A.C. Richardson, in W. Pigman and D. Horton (Eds.), The Carbohydrates, 2nd ed., Vol. 1A, Academic Press, New York, 1972, pp 140-146; J.G. Buchanan, in G. O Aspinall (Ed.), Carbohydrates, MTP International Review of Science, Vol. 7, 1973, pp 37-70.
43. (a) C.H. Marzabadi and C.D. Spilling, J. Org. Chem., 58 (1993) 3761-3766;
44. (b) C.H. Marzabadi, C.D. Spilling, and L.M. Tyler, Tetrahedron, 50 (1994) 6783-6796.
45. C.H. Marzabadi, Reactions of Glucal Halohydrins, Ph.D. dissertation, University of Missouri-St. Louis, 1994.
46. (a) T.W. Greene, Protective Groups in Organic Synthesis, John Wiley and Sons, New York, 1981;
47. (b) K.K. Ogilvie, S.L. Beaucage, D.W. Entwistle, E.A. Thompson, M.A. Quillam, and J.B. Westmore, J. Carbohydr. Nucleosides. Nucleotides., 3 (1976) 197-227;
48. (c) K.K. Ogilvie, Can. J. Chem., 51 (1973) 3799-3807.
49. R.L. Halcomb and S.J. Danishefsky, J. Am. Chem. Soc., 111 (1989) 6661-6666.
50. W.R. Roush, K. Briner, and D.P. Sebesta, Synlett, (1993) 264-266.
51. S.L. Beaucage and K.K. Ogilvie, Tetrahedron Lett., (1977) 1691-1694.
52. T.A.W. Koerner, R.J. Voll, and E.S. Younathan, Carbohydr. Res., 59 (1977) 403-416.
53. a) J.C. Estevez, A.J. Fairbanks, K.Y. Hsia, P. Ward, and G.W.J. Fleet, Tetrahedron Lett., 35 (1994) 3361-3364;
54. (b) J.R. Wheatley, A.R. Beacham, P.M. De Q. Lilley, D.J. Watkin, and G.W.J. Fleet, Tetrahedron: Asymmetry, 5 (1994) 2523-2534.
55. (a) S.J. Mantell, P.S. Ford, D.J. Watkin, G.W.J. Fleet, and D. Brown, Tetrahedron Lett., 33 (1992) 4503-4506;
56. (b) J.C. Estevez, M.D. Smith, A.L. Lane, S. Crook, D.J. Watkin, G.S. Besra, P.J. Brennan, R.J. Nash, and G.W.J. Fleet, Tetrahedron: Asymmetry, 7 (1996) 387-390;
57. J.C. Estevez, M.D. Smith, M.R. Warmold, G.S. Besra, P.J. Brennan, R.J. Nash, and G.W.J. Fleet, Tetrahedron: Asymmetry, 7 (1996) 391-394.
58. R. Lopez and A. Fernandez-Mayoralas, J. Org. Chem., 59 (1994) 737-745.
59. (a) W.P. Griffith, S.V. Ley, G.P. Whitcombe, and A.D. White, J. Chem. Soc., Chem. Commun., (1987) 1625-1627;
60. (b) R. Benhaddou, S. Czernecki, W. Farid, G. Ville, J. Xie, and A. Zegar, Carbohydr. Res., 260 (1994) 243-250.
61. For a review see: Y.A. Zhdanov, Y.E. Alexeev, and V.G. Alexeev, Adv. Carbohydr. Chem. Biochem., 27 (1972) 227-299.
62. K.M. Sun and B. Fraser-Reid, Synthesis, (1982) 28.
63. (a) S. Moutel and J. Prandi, Tetrahedron Lett., 35 (1994) 8163-8166;
64. (b) T. Hosoya, Y. Ohashi, T. Matsumoto, and K. Suzuki, Tetrahedron Lett., 37 (1996) 663-666;
65. (c) M.A. Tius and J. Busch-Petersen, Tetrahedron Lett., 35 (1994) 5181-5184.
66. (a) N.S. Bhacca and D. Horton, J. Am. Chem. Soc., 89 (1967) 5993-5994;
67. (b) P.L. Durette and D. Horton, J. Chem. Soc., Chem. Commun., (1969) 516-518.
68. B. Classon, P.J. Garegg, and B. Samuelsson, Can. J. Chem., 59 (1981) 339-343.
69. (a) V.K. Handa, J.J. Barlow, and K.L. Matta, Carbohydr. Res., 76 (1979) C-1;
70. (b) F.R. Seymour, Carbohydr. Res., 34 (1974) 65-70.
71. G. Ekborg, B. Lindberg, and J. Lönngren, Acta Chem. Scand., 26 (1972) 3287-3292.