Thermal degradation of designed carbohydrate N-oxides: A single methodology for the synthesis of ketoses, enol ethers and branched-chain sugars from N-oxides derived from D-altrose aminosugars

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9715-9718

  Ravindran, Bindu ^a   Pathak, Tanmaya ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; CARBOHYDRATE DERIVATIVE; ETHER DERIVATIVE; KETOSE; OXIDE; PYRANOSIDE; TERTIARY AMINE;

ARTICLE; CHEMICAL REACTION; CONFORMATION; DEGRADATION; DERIVATIZATION; HEATING; METHODOLOGY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033601253     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982199s     Document Type: Article

References (57)

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19. For the synthesis of 6α and 6β, see: (a) Williams, E. H.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1971, 49, 796. (b) Butterworth: R. F.; Hanessian, S. Synthesis 1971, 70. (c) Brewer, C. L.; Guthrie, R. D. J. Chem. Soc., Perkin Trans. 1 1974, 657. (d) Thiem, J.; Rasch, D.; Paulsen, H. Chem. Ber. 1976, 109, 3588. (e) Tsuchiya, T.; Takahashi, Y.; Endo, M.; Umezawa, S.; Umezawa, H. J. Carbohydr. Chem. 1985, 4, 587. (f) Horton, D.; Weckerle, W. Carbohydr. Res. 1988, 174, 305.
20. For the synthesis of 6α and 6β, see: (a) Williams, E. H.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1971, 49, 796. (b) Butterworth: R. F.; Hanessian, S. Synthesis 1971, 70. (c) Brewer, C. L.; Guthrie, R. D. J. Chem. Soc., Perkin Trans. 1 1974, 657. (d) Thiem, J.; Rasch, D.; Paulsen, H. Chem. Ber. 1976, 109, 3588. (e) Tsuchiya, T.; Takahashi, Y.; Endo, M.; Umezawa, S.; Umezawa, H. J. Carbohydr. Chem. 1985, 4, 587. (f) Horton, D.; Weckerle, W. Carbohydr. Res. 1988, 174, 305.
21. For the synthesis of 6α and 6β, see: (a) Williams, E. H.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1971, 49, 796. (b) Butterworth: R. F.; Hanessian, S. Synthesis 1971, 70. (c) Brewer, C. L.; Guthrie, R. D. J. Chem. Soc., Perkin Trans. 1 1974, 657. (d) Thiem, J.; Rasch, D.; Paulsen, H. Chem. Ber. 1976, 109, 3588. (e) Tsuchiya, T.; Takahashi, Y.; Endo, M.; Umezawa, S.; Umezawa, H. J. Carbohydr. Chem. 1985, 4, 587. (f) Horton, D.; Weckerle, W. Carbohydr. Res. 1988, 174, 305.
22. For the synthesis of 6α and 6β, see: (a) Williams, E. H.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1971, 49, 796. (b) Butterworth: R. F.; Hanessian, S. Synthesis 1971, 70. (c) Brewer, C. L.; Guthrie, R. D. J. Chem. Soc., Perkin Trans. 1 1974, 657. (d) Thiem, J.; Rasch, D.; Paulsen, H. Chem. Ber. 1976, 109, 3588. (e) Tsuchiya, T.; Takahashi, Y.; Endo, M.; Umezawa, S.; Umezawa, H. J. Carbohydr. Chem. 1985, 4, 587. (f) Horton, D.; Weckerle, W. Carbohydr. Res. 1988, 174, 305.
23. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
24. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
25. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
26. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
27. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
28. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
29. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
30. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
31. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
32. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
33. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
34. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
35. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
36. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
37. For the applications of 6α and 6β in organic synthesis, see: (a) Hicks, D. R.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1976, 869. (b) Garegg, P. J.; Gotthammar, B. Carbohydr. Res. 1977, 58, 345. (c) Brimacombe, J. S.; Hanna, R.; Marther, A. M.; Weakley, T. J. R. J. Chem. Soc., Perkin Trans. 1 1980, 273. (d) Jarosz, S.; Hicks, D. R.; Fraser-Reid, B. J. Org. Chem. 1982, 47, 935. (e) Tulshian, D. B.; Tsang, R.; Fraser-Reid, B. J. Org. Chem. 1984, 49, 2347. (f) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 77. (g) Krohn, K.; Broser, E.; Heins, H. Carbohydr. Res. 1987, 164, 59. (h) Rocherolle, V.; Lopez, J. C.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 513. (i) Thang, T. T.; Laborde, M. de los A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 1581. (j) Csuk, R.; Furstner, A.; Weidmann, H. J. Carbohydr. Chem. 1986, 5, 271. (k) Peseke, K.; Feist, H.; Cuny, E. Carbohydr. Res. 1992, 230, 319. (l) Feist, H.; Peseke, K.; Koll, P. Carbohydr. Res. 1993, 247, 315. (m) Marschner, C.; Baumgartner, J.; Griengl, H. Liebigs Ann. Chem. 1994, 999. (n) Schmeichel, M.; Redlich, H. Synthesis 1996, 1002. (o) Alves, R. J.; Castillon, S.; Dessinges, A.; Herczegh, P.; Lopez, J. C.; Lukacs, G.; Olesker, A.; Thang, T. T. J. Org. Chem. 1988, 53, 4616.
38. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
39. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
40. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
41. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
42. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
43. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
44. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
45. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
46. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
47. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
48. For the synthesis, biological importance, and synthetic applications of carbohydrate enol ethers, see: (a) Ferrier, R. J.; Prasad, N.; Sankey, G. H. J. Chem. Soc. C 1969, 587. (b) Kelmer, A.; Rodemeyer, G. Chem. Ber. 1975, 108, 1896. (c) Blattner, R.; Ferrier, R. J.; Prasit, P. J. Chem. Soc., Chem. Commun. 1980, 944. (d) Koll, P.; Steinweg, E.; Meyer, B.; Metzger, J. Liebigs Ann. Chem. 1982, 1039. (e) Kong, F.; Su, B. Carbohydr. Res. 1985, 142, 152. (f) Haradahira, T.; Maeda, M.; Kai, Y.; Omae, H.; Kojima, M. Chem. Pharm. Bull. 1985, 33, 165. (g) Varela, O.; de Fina, G. M.; de Lederkermer, R. M. Carbohydr. Res. 1987, 167, 187 (h) Lichtenthaler, F. W.; Ronninger, S.; Jarglis, P. Liebigs Ann. Chem. 1989, 1153. (i) Sigurskjold, B. W.; Duss, B.; Bock, K. Acta Chem. Scand. 1991, 45, 1032. (j) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Org. Chem. 1991, 56, 3054. (k) El Nemr, A.; Tsuchiya, T. Tetrahedron Lett. 1995, 36, 7665. (l) Ichikawa, Y.; Kobayashi, C.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1996, 377.
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