C-disaccharides I. Stereoselective approach to β-(1-4)-3-deoxy-C-disaccharides from levoglucosenone

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2215-2218

  Witczak, Zbigniew J ^a   Chhabra, Renu ^a   Chojnacki, Joanna ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00327-4     Document Type: Article

References (34)

1. 1. Presented in part during XVIIth International Carbohydrate Symposium, Ottawa, Canada, July 17-22, 1994, Abstract No. B1.96; Witczak, Z. J., Abstract Am. Soc. Meet. 208, 1994, : Abstract: CARB. 58.
2. 1. Presented in part during XVIIth International Carbohydrate Symposium, Ottawa, Canada, July 17-22, 1994, Abstract No. B1.96; Witczak, Z. J., Abstract Am. Soc. Meet. 208, 1994, : Abstract: CARB. 58.
3. 2. Witczak, Z. J., in Studies in Natural Products Chemistry, Vol. 3B, Atta-ur-Rahman Ed., Elsevier Science Publishers, Amsterdam, 1989, pp. 209-232; Witczak, Z. J. Pure & Appl. Chem. 1994, 66, 2189-2192.
4. 2. Witczak, Z. J., in Studies in Natural Products Chemistry, Vol. 3B, Atta-ur-Rahman Ed., Elsevier Science Publishers, Amsterdam, 1989, pp. 209-232; Witczak, Z. J. Pure & Appl. Chem. 1994, 66, 2189-2192.
5. 3. a) Witczak, Z. J.; Sun, J.; Mielguj, R., Bioorg.Med.Chem.Lett. 1995, 5, 2169-2174;
6. b) Witczak, Z.J.; Sun, J., Unpublished data
7. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
8. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
9. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
10. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
11. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
12. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
13. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
14. 4. For review see; Postema, M. H. D., Tetrahedron 1992, 48, 8545-8599. For different approaches to (1-4)-C-disaccharides see: Xin, Y. C.; Mallet, J. M.; Sinaÿ, P., J.Chem.Soc. Chem. Commun. 1993, 864-865; Vauzeilles, B.; Cravo, D.; Mallet, J. M.; Sinaÿ, P., Synlett 1993, 522-523; Schmidt, R. R.; Preuss R., Tetrahedron Lett. 1989, 30, 3409-3412; Armstrong, R. W.; Teegarden, B. R., J.Org.Chem., 1992, 57, 915-922; For (1-3)-C-disaccharides synthesis see: Dawson, J. M.; Johnson, T.; Paton, R. M.; Rennie, R. A., J.Chem. Soc.Chem.Commun. 1988, 1339-1340; Preuss, R.; Jung, K.H.; Schmidt, R.R., Liebigs Ann. Chem. 1992, 377-382; Liebigs Ann. Chem. 1992, 983-986.
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