Practical preparation of mono- and di-O-isopropylidene derivatives of monosaccharides and methyl 4,6-O-benzylidene glycosides from free sugars in a deep eutectic solvent

ABSTRACT

Free sugars were rapidly converted into the corresponding di-O-isopropylidene derivatives and methyl O-benzylidene glycosides in excellent yields and purity in a deep eutectic solvent made from choline chloride and malonic acid (ChCl:MA). Reaction conditions were mild; work-up was easy, and further purification was not necessary. Given the inexpensive, nontoxic, and recyclable nature of ChCl:MA, this protocol is environmental friendly.

GRAPHICAL ABSTRACT

A mild and efficient preparation of O-isopropylidene derivatives and methyl 4,6-O-benzylidene glycosides from monosaccharides in a deep eutectic solvent.

KEYWORDS:

• Deep eutectic solvents
• methyl O-benzylidene glycosides
• O-Isopropylidene sugar derivatives

Acknowledgments

The authors thank Mr. Ganesh More and Prof. B. M. Bhanage, Department of Chemistry, Institute of Chemical Technology (ICT), Mumbai, India for facilitating the recording of optical rotations. SMR thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, India for providing a research fellowship. The authors acknowledge work done at ICT in the area of deep eutectic solvents by Dr. G. S. Shankarling, Department of Dyestuff Technology.