Synthesis of isohexide dicarbamates and derivatives thereof

Abstract

Isohexide dicarbamates and a method of preparing the same are described. The method involves reacting a mixture of an isohexide and a cynate salt in a non-aqueous solvent, with a miscible acid having a pKa of about 3.7 or less. The isohexide dicarbamates can serve as precursor materials from which various derivative compounds can be synthesized.

We claim: 
     
         1 . A precursor chemical compound comprising at least one of the following: 
       
         
           
           
               
               
           
         
       
     
     
         2 . A chemical compound derived from at least one of the precursor chemical compounds according to  claim 1 , said derived chemical compound is a polymer containing said precursor chemical compound as a substituent. 
     
     
         3 . The derived chemical compound according to  claim 2 , wherein said polymer is a homopolymer with a structure: 
       
         
           
           
               
               
           
         
       
     
     
         4 . A method of preparing a derivative chemical compound from at least one of the precursor chemical compounds according to  claim 1 , comprising performing a Lewis-acid-(LA)-triflate-mediated N-acylation of isohexide dicarbamates, according to: 
       
         
           
           
               
               
           
         
       
     
     
         5 . The method according to  claim 4 , wherein said Lewis acid triflate is water-tolerant. 
     
     
         6 . The method according to  claim 4 , wherein said derivative chemical compound is at least one of the following: 
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(acetylcarbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(acryloylcarbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(methacryloylcarbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(oleoylcarbamate); 
       
       
         
           
           
               
               
           
         
         (3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(benzoylcarbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis((113-dichloranylidene)carbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis((4-formylphenyl)carbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis((2,2,2-trifluoroacetyl)carbamate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(tert-butylcarbamate); 
       
       
         
           
           
               
               
           
         
         diethyl N′,N″-(W3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyobis(oxy))bis(carbonyl))-(1E,1′E)-diformimidate; 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis((oxo-14-sulfanylidene)carbamate); 
       
       
         
           
           
               
               
           
         
         (3R.3aR.6S.6aR)-hexahydrofuro(3,2-blfuran-3.6-diyl dimethyl bis(carbonate); 
       
       
         
           
           
               
               
           
         
         (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl bis((diaminophosphoryl)carbamate);