5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials

Abstract

A subject of the invention is the compounds of formula (I): in which R represents a carboxylic acid remainder containing up to 18 carbon atoms the products of formula (I) can be used to prepare antibiotic products.

We claim:  
     
       1. A compound of the formula                    
       in which R is an aryl of a carboxylic acid of 1 to 18 carbon atoms. 
     
     
       2. A compound of  claim 1 , in which R is acetyl. 
     
     
       3. A process for the preparation of a compound of  claim 1 , comprising selectively activating the 11-hydroxyl of a compound of the formula                    
       in which R is defined as in  claim 1  with an agent capable of selectively activating the hydroxyl in position 11, reacting the resulting product with a base to obtain the compound of the formula                    
       reacting the latter carbonyldiimidazole, then with hydrazine NH 2 NH 2  to obtain the corresponding compound of formula (I). 
     
     
       4. A process for the preparation of the compound of formula                    
       wherein R′ 1  is selected from the group consisting of hydrogen and an saturated or unsaturated hydrocarbon of up to 23 carbon atoms uninterrupted or interrupted by at least one heteroatom comprising reacting a compound of the formula                                      
       with a cleaving agent for the protected hydroxy functions, then subjecting the resulting product to the reaction with an aldehyde  of the formula                    
       to the reaction with an aldehyde of the formula                    
       wherein R′ 1  has the above definition to obtain a compound of the formula                    
       and subjecting the latter to an oxidizing agent for the 3 hydroxyl group and then to the action of a cleaving agent for the 2′-hydroxyl group to obtain the compound of Formula VII and subjecting the latter to the action of a reducing agent to obtain a compound of formula VIII. 
     
     
       5. The process of  claim 4  wherein R′ 1  has the formula                    
     
     
       6. A compound of the formula                    
       wherein R is an acyl of an organic carboxylic acid of 1 to 18 carbon atoms. 
     
     
       7. A compound of  claim 6  wherein R is acetyl.