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XII. 



THE SYNTHESIS OF GLYCOSIDES: SOME DERIVATIVES 

 OF ARAUmOSE. 



By HUGH RYAN, M.A., D.Sc, F.R.U.I., and 

 GEORGE EBRILL, B.A., Catholic University School of Medicine, 



Dublin. 



Eead June 22, 1903. 



The first experiments recorded in the chemical journals for the syn- 

 thetical preparation of glycosides were made by Schutzenberger.^ 

 From triacetylglucose and the sodium or lead derivatives of saligenin 

 he obtained an amorphous compound, which could be hydrolysed by 

 dilute sulphuric acid into glucose and saliretin, but which was not 

 identical with salicin. In a similar manner a substance, which very 

 closely resembled rhamnegin, was obtained from rhamnetin. 



By the interaction of the acetochloroglucose discovered by Collcy,- 

 and the alkali salts of the phenols, MichaeP obtained helicin, methyl- 

 arbutin and the glucosides of phenol, eugenol, and guaiacol. Using 

 Michael's method, the glucosides of thymol and a-naphthol were 

 obtained by Drouin,* and by a slight modification one of us obtained 

 the glucosides of the three cresols, /S-naphthol, and carvacrol, with 

 the galactoside of a-naphthol, and still later the tetracetyl derivatives 

 of the three cresyl glucosides and of y8-/8-naphthyl giucoside. 



By the condensation of helicin in weak alkaline solution with 

 acetic aldehyde, Tiemannand Kees'' succeeded in obtaining o-cumaric- 

 aldehyde giucoside. Compounds of the aldehydes and ketones with 

 grape-sugar were prepared by Hugo Schiff ^ by the interaction of their 

 components in acetic acid solution. 



' Annalen der Chemie und Physik, clx., p. 95. 

 2 Ann. Chim. Phys., 1870, iv., 21, p. 363. 



^ Comptes Eendus, Ixxxix., p. 355 ; Amer. Chem. Journ., vi., p. 366. 

 * Bull. Soc. Chim., cxi., 13, p. 5. 



5 Kyan, Journ. Chem. Soc, 1899, p. 1051; Eyan and Mills, Journ Chem. 

 See, 1901, p. 704. 



e Proc. Eoyal Dublin Soc, 1901, Vol. ix. (x.s.), iv., p. 503. 

 ' Berichte, xviii. (1885), pp. 1955, 3481. 

 ^ Ann. ccxxiv., p. 19. 



