On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed β-mannopyranosylation and α-glucopyranosylation

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8473-8480

  Crich, David ^a   Vinogradova, Olga ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; IONS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

DIASTEREOSELECTIVITY; GLYCOSYL OXACARBENIUM IONS; GLYCOSYLATION; MANNOSYL DONORS;

CHEMICAL BONDS;

1 BENZENESULFINYLPIPERIDINE; 2 DEOXYARABINOGLYCOSIDE; 3 DEOXYARABINOGLYCOSIDE; 3 DEOXYRIBOTHIOGLYCOSIDE; 4,6 O BENZYLIDENE; ACID ANHYDRIDE; BENZYLIDENE DERIVATIVE; DIPHENYL SULFOXIDE; GLYCOSIDE; ION; MESYLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFOXIDE; TRIFLUOROMETHANESULFONIC ANHYDRIDE; UNCLASSIFIED DRUG;

ALPHA GLUCOPYRANOSYLATION; ARTICLE; BETA MANNOPYRANOSYLATION; CHEMICAL BINDING; CHEMICAL MODIFICATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; GLYCOSYLATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

BENZYLIDENE COMPOUNDS; CARBON; GLUCOSE; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; MOLECULAR STRUCTURE; OXYGEN; STEREOISOMERISM;

EID: 33750439151     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061417b     Document Type: Article

References (62)

1. Crich, D.; Sun, S. J. Org. Chem. 1997, 62, 1198-1199.
2. Crich, D.; Sun, S. Tetrahedron 1998, 54, 8321-8348.
3. Crich, D.; Sun, S. J. Am. Chem. Soc. 1998, 120, 435-436.
4. Crich, D.; Smith, M. J. Am. Chem. Soc. 2001, 123, 9015-9020.
5. Crich, D.; Smith, M. J. Am. Chem. Soc. 2002, 124, 8867-8869.
6. Crich, D.; de la Mora, M.; Vinod, A. U. J. Org. Chem. 2003, 68, 8142-8148.
7. Crich, D.; Cai, W. J. Org. Chem. 1999, 64, 4926-4930.
8. Bousquet, E.; Khitri, M.; Lay, L.; Nicotra, F.; Panza, L.; Russo, G. Carbohydr. Res. 1998, 311, 171-181.
9. Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Jeong, K.-S. Synlett 2003, 1311-1314.
10. Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326.
11. Crich, D.; Jayalath, P. J. Org. Chem. 2005, 70, 7252-7259.
12. Nukada, T.; Berces, A.; Whitfield, D. M. Carhohydr. Res. 2002, 337, 765-774.
13. Lemieux, R. U. In Molecular Rearrangements. Part 2; De Mayo, P., Ed.; Wiley: New York. 1964; pp 709-769.
14. Lucero, C. G.; Woerpel, K. A. J. Org. Chem. 2006, 71, 2641-2647.
15. Smith, D. M.; Woerpel, K. A. Org. Biomol. Chem. 2006, 1195-1201.
16. Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217-11223.
17. Crich, D.; Chandrasekera, N. S. Angew. Chem., Int. Ed. 2004, 43, 5386-5389.
18. Fraser-Reid, B.; Wu, Z. C.; Andrews, W.; Skowronski, E. J. Am. Chem. Soc. 1991, 113, 1434-1435.
19. Andrews, C. W.; Rodebaugh, R.; Fraser-Reid, B. J. Org. Chem. 1996, 61, 5280-5289.
20. Jensen, H. H.; Nordstrom, M.; Bols, M. J. Am. Chem. Soc. 2004, 126, 9205-9213.
21. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
22. Torsion angles were determined with ring conformations fixed according to the parameters provided by Bérces and co-workers (http://www.sao.nrc.ca/ ibs/6ring.html). Bérces, A.; Whitfield, D. M.; Nukuda, T. Tetrahedron 2001, 57, 477-491.
23. Edward, J. T. Chem. Ind. 1955, 1102-1104.
24. Feather, M. S.; Harris, J. F. J. Org. Chem. 1965, 30, 153-157.
25. Overend, W. G.; Rees, C. W.; Sequeira, J. S. J. Chem. Soc. 1962, 3429-3440.
26. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
27. Withers, S. G.; Percival, M. D.; Street, I. P. Carbohydr. Res. 1989, 187, 43-66.
28. Russell, R. N.; Weigel, T. M.; Han, O.; Liu, H.-w. Carbohydr. Res. 1990, 201, 95-114.
29. Classon, B.; Liu, Z.; Samuelsson, B. J. Org. Chem. 1988, 53, 6126-6130.
30. Theander, O. Acta Chem. Scand. 1958, 12, 1883-1885.
31. Barresi, F.; Hindsgaul, O. In Modern Merhods in Carbohydrate Synthesis: Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam. 1996; p 251-276.
32. Pozsgay, V. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, p 319-343.
33. Ito, Y.; Ohnishi, Y. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B., Kuniaki, T., Thiem, J., Eds.; Springer-Verlag: Berlin, 2001; Vol. 2, p 1589-1619.
34. Lichtenthaler, F. W.; Lergenmüller, M.; Peters, S.; Varga, Z. Tetrahedron: Asymmetry 2003, 14, 727-736.
35. Ekborg, G.; Lindberg, B.; Lonngren, J. Acta Chem. Scand. B 1972, 26, 3287-3292.
36. Dess, P. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
37. Roush, W. R.; Sebesta, D. P.; Bennett, C. E. Tetrahedron 1997, 53, 8825-8836.
38. Crich, D.; Ritchie, T. J. J. Chem. Soc., Perkin Trans. 1 1990, 945-954.
39. 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.
40. Codée, J. D. C.; Litjens, R. E. J. N.; Van den Bos, L. J.; Overkleeft, H. S.; Van der Marel, G. Chem. Soc. Rev. 2005, 34, 769-782.
41. Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269-4279.
42. Crich, D.; Hutton, T. K.; Banerjee, A.; Jayalath, P.; Picione, J. Tetrahedron: Asymmetry 2005, 16, 105-119.
43. Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293-297.
44. Duus, J. O.; Gotfredsen, C. H.; Bock, K. Chem. Rev. 2000, 100, 4589-4614.
45. Thiem, J.; Klaffke, W. Topics Curr. Chem. 1990, 154, 285-332.
46. Marzabadi, C. H.; Franck, R. W. Tetrahedron 2000, 56, 8385-8417.
47. Veyrières, A. In Carbohydrates in Chemistry and Biology, Ernst, B., Hart, G. W., Sinay, P., Eds.: Wiley-VCH: Weinheim, 2000; Vol. 13, pp 367-405.
48. Green, L. G.; Ley, S. V. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, pp 427-448.
49. Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753.
50. Namchuk, M. N.; McCarter, J. D.; Becalski, A.; Andrews, T.; Withers, S. G. J. Am. Chem. Soc. 2000, 122, 1270-1277.
51. Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
52. Gildersleeve, J.; Smith, A.; Sakurai, D.; Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 6176-6182.
53. Hashimoto, S.; Sano, A.; Sakamoto, H.; Nakajima, M.; Yanagiya, Y.; Ikegami, S. Synlett 1995, 1271-1273.
54. Bock, K.; Pedersen, H. Acta Chem. Scand. 1987, B41, 617-628.
55. van Dorst, J. A. L. M.; van Heusden, C. J.; Tikkanen, J. M.; Kamerling, J. P.; Vliegenthart, J. F. G. Carbohydr. Res. 1997, 297, 209-227.
56. Oscarson, S.; Svahnberg, P. Carbohydr. Res. 1998, 309, 207-212.
57. Oscarson, S.; Tedebark, U. Carbohydr. Res. 1995, 278, 271-287.
58. Kováč, P.; Edgar, K. J. Carbohydr. Res. 1990, 201, 79-83.
59. Richards, G. N. Chem. Ind. 1955, 228-228.
60. Crich, D.; Cai, W.; Dai, Z. J. Org. Chem. 2000, 65, 1291-1297.
61. Crich, D.; Vinod, A. U.; Picione, J.; Wink, D. J. ARKIVOC 2005, (vi), 339-344.
62. Crich, D.; Vinod, A. U.; Picione, J. J. Org. Chem. 2003, 68, 8453-8458.