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Regioselective monotosylation, for the first time on 2,4-syn & 2,4-anti configured ene-tetrols and on diols & triols was achieved in excellent yields and selectivity by employing [DMAPTs] + Cl À , 1. We also proposed and developed operational flexible preferential regio-complimentary tosylation of cis-1,2-diol moiety of pyranosides by employing 1. Further NMR correlation for unambiguous structure determination of regioselectivity and also preferred conformations of these pyranosides were established.

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N-benzoyl-4-dimethylaminopyridinium chloride [DMAPBz] + Cl À was efficiently employed for polybenzoylation of triols and tetrols without epimerization and elimination products. This Lewis base adduct has also been employed for regioselective monobenzoylation of polyols obtained from D-pentoses. Fur-ther an eco-friendly monobenzoylation of phenols, amines and alcohols was achieved in water as a solvent without using a base and chromatographic purification of the products. Chemoselective monobenzoylation and recovery of the DMAP is an added advantage of our protocol.