Novel syntheses of diphenyl and/or trimethylene dithioacetals of mono- and oligosaccharides in 90% trifluoroacetic acid

Journal of Carbohydrate Chemistry

Volumn 18, Issue 3, 1999, Pages 333-341

  Funabashi, Masuo ^a   Arai, Sachiko ^a   Shinohara, Masashi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033475148     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309908543999     Document Type: Article

References (14)

1. J. D. Wanderand D. Horton, Adv. Carbohydr. Chem. Biochem., 32, 15 (1976).
2. a) M. L. Wolfrom, M. R. Newlin , and E. E. Stahly, J. Am. Chem. Soc., 83, 4379 (1931).
3. b) P. V. Eikeren, W. A. White, and D.M. Chipman, J. Org.Chem., 38, 1831 (1973).
4. a) E. Fischer, Ber., 27, 673 (1894),
5. b) E. Fischer, Untersuchungen über Kohlenhydrate und Fermente , Verlag von Julius Springer,1909, p 89.
6. E. Zisis, A. L. Clingman, and N. K. Richtmyer, Carbohydr. Res., 2, 461 (1966).
7. D. Horton and J. D. Wander, Carbohydr. Res., 13, 33 (1970), ibid., 15, 271 (1970).
8. D. Horton and J. D. Wander, Carbohydr. Res., 13, 33 (1970), ibid., 15, 271 (1970).
9. a) O. Kölln and H. Redlich, Synthesis, 1376 (1995).
10. b) O. Kölln, H. Redlich, and H. Frank, ibid., 1383 (1995).
11. O. Kölln and H. Redlich, ibid., 826 (1996).
12. The acyclic form of 2-acetamido-2-deoxy-D-glucose was proposed in trifluoroacetic acid: M. Ranaganathan, V.S.R. Rao, and P. Balaram, Carbohydr. Res., 58, 245 (1977).
13. 1H NMR spectrum of D-lyxose diphenyl dithioacetal 2,3,4,5-letraacetate was in good accord with the reported spectrum (ref. 4).
14. Purification of free oligosaccharide diphenyldithioacelals except maltose diphenyl dithioacelal was unexpectedly difficult, because 1-butanol used for extraction could not completely be removed even in vacua from the dithioacetals.