II. CHEMISTRY 



415 



presence of amnionium chloride. (Uycosides were prepared from D-glucose, 

 D-mannose, D-galactose, L-arabinose, D-xylose, D-ribose, and L-rhamnose as 

 sugars; the agh'cones wei'e o-nitroaniline, w-nitro-p-toluidine, 3- and 5- 

 nitro-o-4-xyHdines.^^ The glycosides formed in this reaction were usually a 

 mixture of two isomers; these were acetylated and subjected to catalytic 

 reduction as shown below for the glucoside. 



-0 





OAc H 



H I I 



c— c c- 



H OAc H 

 NH 



OAc 



C C— CH2OAC 



H 



NO2 



O- 



OAc H 



H I I 



c— c c- 



H OAc H 

 NH 



NH, 



OAc 



I 

 C — 



-C— CH2OAC 

 H 



Reduction of certain isomeric mixtures brought about the formation of 

 a single compound. Treatment with ethyl orthoformate gave the cor- 



-0 



/\/ 



OAc H OAc 

 Hill 

 C— C C C C— CH2OAC 



H OAc H H 



NH 



HCl 



N=CHOC2H5 



C C C— CH2OAC 



H OAc H H 



