Disaccharide synthesis on a soluble hyperbranched polymer

Tetrahedron Letters

Volumn 40, Issue 46, 1999, Pages 8049-8053

  Kantchev, Assen B ^a   Parquette, Jon R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Carbohydrates; Hyperbranched polymer; Oligosaccharides; Solution phase synthesis

Indexed keywords

DISACCHARIDE; POLYMER;

ARTICLE; CHEMICAL ANALYSIS; SOLUBILITY; SYNTHESIS;

EID: 0033550242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01709-8     Document Type: Article

References (27)

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10. For a dendritically expanded Tentagel resin, see: (a) Swali, V.; Wells, N. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1997, 62, 4902. (b) Wells, N. J.; Davies, M.; Bradley, M. J. Org. Chem. 1998, 63, 6430. For a PEG resin with increased loading capacity, see: (b) Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Ressel, S. J. Org. Chem. 1998, 63, 8628. (c) Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706.
11. For a dendritically expanded Tentagel resin, see: (a) Swali, V.; Wells, N. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1997, 62, 4902. (b) Wells, N. J.; Davies, M.; Bradley, M. J. Org. Chem. 1998, 63, 6430. For a PEG resin with increasedloading capacity, see: (b) Benaglia, M.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Ressel, S. J. Org. Chem. 1998, 63, 8628. (c) Adams, J. H.; Cook, R. M.; Hudson, D.; Jammalamadaka, V.; Lyttle, M. H.; Songster, M. F. J. Org. Chem. 1998, 63, 3706.
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18. A 40% loading level was chosen to provide an intermediate density of substrates on the support; however, higher loading levels have not yet been investigated.
19. The polymer loading was determined by proton NMR spectroscopy using DMF as an internal standard.
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21. Preparation of thioglycoside 10: (a) Zhang, Y.-M.; Mallet, J. M.; Sinay, P. Carbohydr. Res. 1992, 236, 73. 11: (b) Haellgren, C.; Hindsgaul, O. Carbohydr. Res. 1994, 260, 63. 14: (a) Sarbajna, S.; Misra, A. K.; Roy, N. Synth. Commun. 1998, 28, 2559. 15: (b) Boons, G. J.; Grice, P.; Leslie, R.; Ley, S. V.; Yeung, L. Tetrahedron Lett. 1993, 34, 8523.
22. Preparation of thioglycoside 10: (a) Zhang, Y.-M.; Mallet, J. M.; Sinay, P. Carbohydr. Res. 1992, 236, 73. 11: (b) Haellgren, C.; Hindsgaul, O. Carbohydr. Res. 1994, 260, 63. 14: (a) Sarbajna, S.; Misra, A. K.; Roy, N. Synth. Commun. 1998, 28, 2559. 15: (b) Boons, G. J.; Grice, P.; Leslie, R.; Ley, S. V.; Yeung, L. Tetrahedron Lett. 1993, 34, 8523.
23. Preparation of thioglycoside 10: (a) Zhang, Y.-M.; Mallet, J. M.; Sinay, P. Carbohydr. Res. 1992, 236, 73. 11: (b) Haellgren, C.; Hindsgaul, O. Carbohydr. Res. 1994, 260, 63. 14: (a) Sarbajna, S.; Misra, A. K.; Roy, N. Synth. Commun. 1998, 28, 2559. 15: (b) Boons, G. J.; Grice, P.; Leslie, R.; Ley, S. V.; Yeung, L. Tetrahedron Lett. 1993, 34, 8523.
24. Review: Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
25. 12; C, 72.71; H, 6.54. Found: C, 72.54; H, 6.57.
26. 1H NMR.
27. 15; C, 70.31; N, 1.30; H, 6.09. Found: C, 70.20; N, 1.35; H, 6.13.