Synthesis, and Spectral Characterization of 6-O-Octanoyl-1,2-O-isopropylidene-α-D-glucofuranose Derivatives

Year 2021, Volume: 8 Issue: 4, 1003 - 1024, 30.11.2021

Puja Devi , Mohammed Mahbubul Matin , Md. Mosharef Hossain Bhuiyan , Md. Emdad Hossain

https://doi.org/10.18596/jotcsa.929996

Cited By: 1

Abstract

Site selective acylation of monosaccharides and oligosaccharides are very necessary for the preparation of both natural and novel synthetic carbohydrate compounds, synthetic intermediates, postglycosylation modifications, and for the preparation of therapeutic agents including research tools for glycobiology. Hence, site selective octanoylation of 1,2-O-isopropylidene-α-D-glucofuranose was conducted. Under low temperature in anhydrous pyridine direct unimolar octanoylation of this glucofuranose without any catalyst exhibited selectivity at C-6 hydroxyl group. The C-6 O-octanoylglucofuranose, thus obtained, was then used for the preparation of three 3,5-di-O-acyl esters in a similar direct method to get novel esters of glucofuranose. Characterization of all the glucofuranose esters by 1D and 2D spectroscopic technique is also discussed herein.

Keywords

Bisacetone D-glucose, HMBC, Site selective acylation, Sugar esters

Supporting Institution

Ministry of Science and Technology, Bangladesh

Project Number

Phys 535, 2020-21

Thanks

We are grateful to the Ministry of Science and Technology, Bangladesh for financial support (Phys 535, 2020-21) to conduct this research work.

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