Novel synthesis of galactoside inhibitors

Abstract

Novel synthesis routes for preparation of thiodigalactosides and intermediates are presented. The method includes the use of a 3-azido-galactosyl thiouronium salt derivative, which is activated to the corresponding thiol in situ, which in turn is directly reacted with a 3-azido-galactosyl bromide resulting in the 3,3′-di-azido-thio-di-galactoside before the thiol has a chance to reduce the azido 10 group. Hence, in situ formation of the 3-azido-galactosyl thiol from the thiouronium salt is essential in the synthesis procedure, because any other method that generate the thiol separately results in extensive unwanted azide reduction.

1 . A compound of the formula (14) 
       
         
           
           
               
               
           
         
       
       wherein R is one or more trifluoromethyl, preferably in meta and/or para position. 
     
     
         2 . The compound of  claim 1  wherein R is one trifluoromethyl. 
     
     
         3 . The compound of  claim 1  wherein R is two trifluoromethyl. 
     
     
         4 . The compound of  claim 2  wherein R is in meta position. 
     
     
         5 . The compound of  claim 2  wherein R is in para position. 
     
     
         6 . The compound of  claim 3  wherein R is in meta and para position.