PURDIE'S REACTION 207 



remains unaltered after several treatments with silver oxide 

 and methyl iodide, and therefore has the formula 



CH 3 . CH 2 . CH(OCH 3 ) . CH . CH(OCH 3 ) . CH(OCH 3 ) . CH . NHC 6 H 5 . 



' 



Glucoseanilide is prepared in the same way as its tetramethyl 

 analogue, and in its preparation and mutarotation Irvine 

 and Gilmour (42) have obtained evidence of the existence of 

 two stereoisomeric forms of the substance. Methylation of 

 the compound (a matter of great difficulty by reason of its 

 susceptibility to oxidation) led to the formation of a crystal- 

 line tetramethyl glucoseanilide, identical with that prepared 

 as above. The constitution of glucoseanilide is thus estab- 

 lished, and shown to be represented by the formula 



(HO) . CH 2 . CH(OH) . CH . CH(OH) . CH(OH) . CH . NH . C 6 H 5 . 







(a- and /3-fonns) 



It may be mentioned that the optical values for the two 

 anilides obey Hudson's Law. Irvine and McNicoll (56) have 

 extended this work to the anilides of tetramethyl mannose, 

 tetramethyl galactose, and trimethyl rhamnose, and further, 

 to the anilides of the parent unmethylated sugars, mannose, 

 galactose, and rhamnose. Their results are in every way 

 comparable with those described above. 



Similar methods and reasoning have been adopted by 

 Irvine and Moodie (41) and Irvine and Gilmour (42) in their 

 work on glucoseoxime, which appears to be capable of reacting 

 according to the structure 



HO . CH 2 . CH(OH) . CH . CH(OH) . CH(OH) . CH . NH . OH. 







(a- and /9-forms) 



