A Facile Synthetic Approach for Alkyl α-Glycosides of Reducing Disaccharides

Chemical and Pharmaceutical Bulletin

Volumn 26, Issue 5, 1978, Pages 1570-1575

  Gi, Chung Tai ^a   Ishihara, Hideko ^a   Tejima, Setsuzo ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

benzyl glycosides formation of reducing disaccharides; benzyl maltoside heptaacetate; GLC analysis of anomeric glycosides; methyl glycosides formation of reducing disaccharides; methyl lactoside; NMR; glycosyl N,N dimethyldithiocarbamates

Indexed keywords

EID: 85004637503     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.26.1570     Document Type: Article

References (26)

1. R.U. Lemieux, T.L. Nagabhushan, K.J. Clemetson, and L.C.N. Tucker, Can. J. Chem., 51, 53 (1973);
2. F.J. Kronzer and C. Schuerch, Carbohyd. Res., 33, 273, 34, 71 (1974);
3. R. Eby and C. Schuerch, Carbohyd. Res., 34, 79 (1974);
4. J.M. Berry and G.G.S. Dutton, Carbohyd. Res., 38, 339 (1974);
5. K. Igarashi, J. Irisawa, and T. Honma, Carbohyd. Res., 39, 341 (1975);
6. R.U. Lemieux, K.B. Hendriks, R.V. Stick, and K. James, J. Am. Chem. Soc., 97 4056 (1975).
7. S. Tejima and S. Ishiguro, Chem. Pharm. Bull. (Tokyo), 15, 255 (1967).
8. P.G. Scheurer and F. Smith, J. Am. Chem. Soc., 76, 3224 (1954).
9. M. Mori, M. Haga, and S. Tejima, Chem. Pharm. Bull. (Tokyo), 22, 1331 (1974).
10. G. Zemplèn and A. Gerecs, Ber., 63, 2720 (1930).
11. R.J. Ferrier, R.W. Hay, and N. Vethaviyasar, Carbohyd. Res., 27, 55 (1973).
12. K. Takeo, Carbohyd. Res., 48, 290 (1976).
13. aE. Pacsu, J. Am. Chem. Soc., 52, 2571 (1930);
14. bB. Helferich and W. Piel, Ann. Chem., 623, 124 (1959).
15. P.W. Austin, F.E. Hardy, J.G. Buchanan, and J. Baddiley, I. Chem. Soc., 1963, 5350.
16. A. Hasegawa, N. Kurihara, D. Nishimura, and M. Nakajima, Agr. Biol. Chem., 32, 1130 (1968).
17. K. Takeo, K. Mine, and T. Kuge, Carbohyd. Res., 48, 197 (1976).
18. C.C. Sweeley, R. Bentley, N. Makita, and W.W. Wells, J. Am. Chem. Soc., 85, 2497 (1963).
19. F. Smith and J.W. Van Cleve, J. Am. Chem. Soc., 74, 1912 (1952).
20. W.E. Dick, Jr., D. Weisleder, and J.E. Hodge, Carbohyd. Res., 18, 115 (1971).
21. M.L. Wolfrom, Y.-L. Hung, P. Chakravarty, G.U. Yuen, and D. Horton, J. Org. Chem., 31, 2227 (1966).
22. J.C. Irvine and I.M.A. Black, J. Chem. Soc., 1926, 862.
23. Y. Hirasaka, Yakugaku Zasshi, 83, 960 (1963).
24. H. Fischer and F. Kögl, Ann. Chem., 436, 219 (1924).
25. G. Jayme and W. Demmig, Chem. Ber., 93, 356 (1960).
26. N.K. Richtmyer, J. Am. Chem. Soc., 68, 1136 (1946).