Stereoselective synthesis of β-mannopyranosides via the temporary silicon connection method

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 247-248

  Stork, Gilbert ^a   La Clair, James J ^a,b  

^a Columbia University ^*  (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030023578     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9532291     Document Type: Article

References (49)

1. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
2. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
3. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
4. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
5. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
6. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
7. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
8. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
9. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
10. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
11. For a survey of the chemical synthesis of β-mannopyranosides, see: (a) Gorin. P. A. J.; Perlin, A. S. Can. J. Chem. 1969, 39, 2474. (b) Betaneli, V. I.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1980, 84. 211, 225. (C) Paulsen, H.; Kutsehker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3102, 3233. (d) Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121 (e) Garegg, P. J., Ossowski, P. Acta Chem. Scand. 1983, B37, 229. (f) Rathmore, H.; From, A. H. L.; Ahmed, K.; Fullerton, D. S. J. Med. Chem. 1986, 29, 1945. (g) Gunther, W.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1050. (h) Yamazaki, N.; Eichenberger. E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623. (i) Brunckova, J.; Crich. D.; Yao, Q. Tetrahedron Lett. 1994, 35, 6619. (j) Liu, K. C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (k) Lichtenthaler, F. W.; Schneider Adams, Th.; Immel, S. J. Org. Chem. 1994, 59, 6735.
12. Stork, G.; Mook. R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
13. Stork, G.; Sher, P. M.; Chen, H. L. J. Am. Chem. Soc. 1986, 108, 6384
14. Stork, G.; Sofia, M. J. J. Am. Chem. Soc. 1986, 108, 6826.
15. (a) De Mesmaeker, A.; Hoffmann, P.; Ernst, B.; Hug, P., Winkler, T. Tetrahedron Lett. 1988, 29, 6585.
16. (b) De Mesmaeker, A.; Hoffmann, P.; Ernst, B. Tetrahedron Lett. 1989, 30, 57.
17. (c) De Mesmaeker, A.; Hoffmann, P.; Ernst, B ; Hug, P.; Winkler, T. Tetrahedron Lett. 1989, 30, 6307.
18. (d) De Mesmaeker, A.; Hoffmann, P.; Winkler, T.; Waldner, A. Synlett 1990, 201.
19. (e) De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687.
20. (f) De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Hug, P., Winkler, T. Synlett 1992, 285.
21. (g) De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Winkler, T. Synlett 1994, 330.
22. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. See also: (a) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991. 113, 9661. (b) Xin, Y. C.; Mallet, J -M.; Sinaÿ. P. J. Chem. Soc., Chem. Commun. 1993, 864. (c) Chenede, A.; Perry, E.; Rekai, E. D.; Sinay, P. Synlett 1994, 420.
23. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. See also: (a) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991. 113, 9661. (b) Xin, Y. C.; Mallet, J -M.; Sinaÿ. P. J. Chem. Soc., Chem. Commun. 1993, 864. (c) Chenede, A.; Perry, E.; Rekai, E. D.; Sinay, P. Synlett 1994, 420.
24. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. See also: (a) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991. 113, 9661. (b) Xin, Y. C.; Mallet, J -M.; Sinaÿ. P. J. Chem. Soc., Chem. Commun. 1993, 864. (c) Chenede, A.; Perry, E.; Rekai, E. D.; Sinay, P. Synlett 1994, 420.
25. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054. See also: (a) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991. 113, 9661. (b) Xin, Y. C.; Mallet, J -M.; Sinaÿ. P. J. Chem. Soc., Chem. Commun. 1993, 864. (c) Chenede, A.; Perry, E.; Rekai, E. D.; Sinay, P. Synlett 1994, 420.
26. (a) Barresi, F.; Hindsgaul, O. J. Am. Chem. Soc. 1991, 112, 9376.
27. (b) Barresi. F.; Hindsgaul, O. Synlett 1992, 795.
28. (c) Barresi, F.; Hindsgaul, O. Can. J. Chem. 1994, 72, 1447.
29. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087. See also: (a) Bols, M. Tetrahedron 1993, 49, 10049. (b) Bols, M. Acta Chem. Scand. 1993, 47, 829.
30. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087. See also: (a) Bols, M. Tetrahedron 1993, 49, 10049. (b) Bols, M. Acta Chem. Scand. 1993, 47, 829.
31. Stork, G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087. See also: (a) Bols, M. Tetrahedron 1993, 49, 10049. (b) Bols, M. Acta Chem. Scand. 1993, 47, 829.
32. (a) Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765.
33. (b) Dan, A.; Ito, Y.; Ogawa, T. J. Org. Chem. 1995, 60, 4680.
34. (a) Kahne, D.; Walker, S.; Cheng, Y.; Van Enaen, D. J. Am. Chem. Soc. 1989, 111, 6881
35. (b) Hamilton-Andreotti, A.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 3352.
36. (c) Ragahvan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580.
37. (d) Yan, L.; Taylor. C. M.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6853.
38. Only one sulfoxide diastereomer was produced (in 89% yield) by oxidation of the corresponding sulfide with m-CPBA. See ref 7 for the synthesis of the sulfide precursor to 3.
39. For example, a mixture of 1 equiv of imidazole, 0.5 equiv each of DMAP, mannose sulfoxide 3, and β-methyl glucoside 6 (THF at -78 °C), treated with 0.5 equiv of dichlorodimethylsilane, gave 84% of the corresponding tethered species (cf. 4). Addition of 2 equiv of triflic anhydride to the above in ether - methylene chloride (-100 °C) then gave 12 (65%, after flash Chromatography). See supporting information for more details. The success of this procedure derives from the slower silylation of the 2-hydroxyl derivative of mannose sulfoxide 3 than of the free hydroxyl of the glucose derivative in the cases we have examined. The exact reason is not firmly established.
40. Methyl glucoside 6 was prepared from 3,4,6-tribenzvlglucal using the method of: Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
41. Koto, S.; Morishima, R.; Kawahara, K.; Ishikawa, K.; Zen, S. Bull. Chem. Soc. Jpn. 1982, 55, 631.
42. 5 hydrogens strongly supports the β-stereochemistry of mannosides 12. 13, and 15. An additional NOE between the anomeric hydrogen and the proximal hydrogen on the glucosidic moiety provided further support for the assigned connectivity.
43. Yields for both steps of the method as well as the overall recovery of disaccharide are tabulated below: substrate tethering glycosylation overall 5 89% 92% 82% 6 84% 65% 55% 7 88% 82% 72% 8 98% 12%* 12% 9 60% 48% 29% 10 78% 54%* 42% *The remaining material underwent 6-O-debenzylation (i.e., to 18).
44. Garegg, P. J.; Iversen, I.; Oscarson, S. Carbohydr. Res. 1976, 50, C12.
45. 1H NMR spectra of this product matched that reported by Hindsgaul (see ref 7c).
46. Triflation of 17 produced 12% of 14, 82% of 18, and 4% of the α-anomer of 18. Changing the protecting groups about the mannose substituent (i.e., methyl instead of benzyl ethers) did not alter the outcome of this process.
47. 5, and anomeric hydrogens within the mannose substituent).
48. Stevens, C. L.; Blumbergs, P.; Otterbach, D. H. J. Org. Chem. 1966, 31, 2817.
49. Glycosylanon of the silaketal from 10 was accompanied by production of 41% of its 6-O-debenzylated product.