Regioselective Synthesis of Some Rhamnopyranoside Esters for PASS Predication, and ADMET Studies

Notable biological activities including brains protective have made carbohydrate esters as a topic of great interest over the past several decades. In this context, unimolecular treatment methyl α-L-rhamnopyranoside (3) with dibutyltin oxide gave corresponding 2,3-O-(dibutylstannylene) derivative which was then allowed to react 3-chlorobenzoyl chloride. The reaction regioselectively furnished 3-O-substitution product 4 in excellent yield. To get newer rhamnopyranoside chlorobenzoate further converted into four 2,4-di-O-substituted products 5-8 other acylating agents using direct acylation technique. Moreover, thermodynamic properties indicated that these SEs possess better stability, suitable polar nature and higher binding affinity than non-ester 3. PASS (Prediction Activity Spectra for Substances) predication showed should be more potent against fungal pathogens bacterial organisms. With encouraging results ADMET drug-likeness 4-8 are also discussed.