Synthesis of sterically crowded derivatives of anomeric pairs of D-glucose disaccharides

Carbohydrate Research

Volumn 340, Issue 12, 2005, Pages 2055-2059

  Mendonca, Sanford ^a   Laine, Roger A ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

Derivatized disaccharides; Glucose

Indexed keywords

CARBOHYDRATES; MASS SPECTROMETRY; POLYSACCHARIDES; SYNTHESIS (CHEMICAL);

ANOMERIC CONFIGURATION; STEREO-ISOMERIC GLUCOSE;

GLUCOSE;

CARBOHYDRATE DERIVATIVE; CELLOBIOSE; DISACCHARIDE; GENTIOBIOSE; ISOMALTOSE; MALTOSE; SOPHOROSE; TREHALOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL BOND; DERIVATIZATION; FRAGMENTATION REACTION; MASS SPECTROMETRY; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURE ANALYSIS;

ACETYLATION; ALKYLATION; CELLOBIOSE; DISACCHARIDES; ISOMALTOSE; MALTOSE; STEREOISOMERISM;

EID: 22744445032     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2005.05.016     Document Type: Article

References (33)

1. J.F.W. McOmoie Protective Groups in Organic Chemistry 1973 Plenum Press London
2. R.A. Laine, K. Pamidimukkala, A.D. French, R.W. Hall, S.A. Abbas, R.K. Jain, and K.L. Matta J. Am. Chem. Soc. 110 1988 6931 6939
3. P.J. Stoffyn, and R.W. Jeanloz J. Biol. Chem. 235 1960 2507 2510
4. R.W. Jeanloz G.F. Springer Polysaccharide in Biology 1958 The Josiah Macy Jr. Foundation New York 23 (fourth conference)
5. R. Kuhn, H. Trischmann, and I. Löw Angew. Chem. 67 1955 32 36
6. T. Yamakawa, S. Yokoyama, and N. Handa J. Biochem. 53 1963 28 35
7. F. Leung, and R.H. Marchessault Can. J. Chem. 51 1973 1215 1222
8. F. Leung, D. Chanzy, S. Pérez, and R.H. Marchessault Can. J. Chem. 54 1976 1365 1371
9. H. Takeda, T. Kaiya, N. Yasuoka, and N. Kasai Carbohydr. Res. 62 1978 27 37
10. S. Pérez, and F. Brisse Acta Crystallogr. Sect. B 33 1977 2578 2584
11. S. Pérez, J. St.-Pierre, and R.H. Marchessault Can. J. Chem. 56 1978 2866 2871
12. F. Brisse, R.H. Marchessault, S. Pérez, and P. Zugenmaier J. Am. Chem. Soc. 104 1982 7470 7476
13. S. Pérez, C. Vergelati, and V.H. Tran Acta Crystallogr., Sect. B 41 1985 262 267
14. R.H. Marchessault, and P.R. Sundarajan G.O. Aspinall The Polysaccharides Vol. 2 1979 Academic Press New York
15. R.C.W. Berkeley C.W. Gooday D.C. Ellwood Microbial Polysaccharides and Polysacharases 1979 Academic Press New York
16. T. Purdie, and J.C. Irvine J. Chem. Soc. 83 1903 1021 1037
17. W.N. Haworth J. Chem. Soc. 107 1915 8 16
18. S. Mendonca, R.B. Cole, J. Zhu, Y. Cai, A.D. French, G.P. Johnson, and R.A. Laine J. Am. Soc. Mass Spectrom. 14 2003 63 78
19. H.G. Walker, M. Gee, and R.M. Mcready J. Org. Chem. 27 1962 2100 2102
20. R. Kuhn, H.H. Baer, and A. Seeliger Justus Liebigs Ann. Chem. 611 1958 236 241
21. Z. Tamura, and T. Imanari Chem. Pharm. Bull. 12 1964 1386 1391
22. E.J. Corey, and M. Chaykovsky J. Am. Chem. Soc. 84 1962 866 867
23. M. Chaykovsky, and E.J. Corey J. Org. Chem. 28 1962 254 255
24. R. Greenwald, M. Chaykovsky, and E.J. Corey J. Org. Chem. 28 1962 1128 1129
25. S. Hakomori J. Biochem. 55 1964 205 208
26. J.J. Brauman, A. Bryson, D.C. Kahl, and N.J. Nelson J. Am. Chem. Soc. 92 1970 6679 6680
27. B. Lindberg Methods Enzymol. 28 1972 178 195
28. J. Finne, T. Krusius, and H. Rauvala Carbohydr. Res. 80 1980 336 339
29. I. Ciucanu, and F. Kerek Carbohydr. Res. 131 1984 209 217
30. C.S. Hudson, and D.H. Brauns J. Am. Chem. Soc. 37 1915 1264 1270
31. E.J. Corey, and A.K. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190 6191
32. E.J. Corey, H. Cho, C. Rucker, and D.H. Rucker Tetrahedron Lett. 22 1981 3455 3458
33. S. Mendonca, G.P. Johnson, A.D. French, and R.A. Laine J. Phys. Chem. A 106 2002 4115 4124