Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1947-1950

  Codée, Jeroen D C ^a   Van Den Bos, Leendert J ^a   Litjens, Remy E J N ^a   Overkleeft, Herman S ^a   Van Boom, Jacques H ^a   Van Der Marel, Gijs A ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; EPITOPE; HYALURONIC ACID DERIVATIVE; THIOGLYCOSIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; TRISACCHARIDE;

ARTICLE; GLYCOSYLATION; POLYMERIZATION; QUANTUM YIELD; SYNTHESIS; CARBOHYDRATE ANALYSIS; MOLECULAR GENETICS;

CARBOHYDRATE SEQUENCE; GLYCOSYLATION; INDICATORS AND REAGENTS; MOLECULAR SEQUENCE DATA; TRISACCHARIDES;

EID: 0042853252     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034528v     Document Type: Article

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34. 2O-activated systems.
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39. Occurrence of this possibility is endorsed by the following experiment: premixing the disarmed thiodonor ethyl 2,3,4,6-tetra-O-benzoyl-1-thioglucopyranoside and the reactive acceptor α-O-methyl-2,3,4-tri-O-benzyl glucose and subsequent treatment of this mixture with 1.0 equiv of the less reactive 2b led to quantitative recovery of the donor glycoside and isolation of the acceptor-6-O-benzenesulfinyl piperidine triflate adduct in 96% yield.
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47. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
48. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
49. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
50. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
51. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
52. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
53. For previous syntheses of the α-Gal epitope, see: (a) Garegg, P.; Oscarson, S. Carbohydr. Res. 1985, 136, 207-213. (b) Schaubach, R.; Hemberger, J.; Kinzy, U. Liebigs Ann. Chem. 1991, 607-614. (c) Reddy, G. V.; Jain, R. K.; Bhatti, B. S.; Matta, K. L. Carbohydr. Res. 1994, 263, 67-77. (d) Vic, G.; Tran, C. H.; Scigelova, M.; Crout, D. H. G. Chem. Commun. 1997, 167-170. (e) Nilsson, K. G. I. Tetrahedron Lett. 1997, 38, 133-136. (f) Fang, J.; Li, J.; Chen, X.; Zhang, X.; Wang, J.; Guo, Z.; Zhang, W.; Yu, L.; Brew, K.; Wang, P. G. J. Am. Chem. Soc. 1998, 120, 6635-6638. (g) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; Duthaler, R. O.; Katopodis, A.; Streiff, M. B.; Kinzy, W.; Oehrlein, R. Tetrahedron 2001, 57, 3281-3290.
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56. For a recent review, see: (a) Yeung, B. K. S.; Chong, P. Y. C.; Petillo, P. A. J. Carbohydr. Chem. 2002, 21, 799-865. (b) Glycochemistry: Principles, Synthesis, and Applications; Wang, P. G., Bertozzi, C. R., Eds.; Marcel Dekker: New York, 2001; pp 425-492.
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58. Several syntheses of hyaluronan oligosaccharides avoid the use of glucuronic acid building blocks for this reason. Alternatively, glucopyranose building blocks are employed that are orthogonally protected on the 6-position, which after deprotection is oxidized at the end of the synthesis. See ref 20.