Hydroboration-oxidation: A chemoselective route to cellulose ω-hydroxyalkanoate esters

Carbohydrate Polymers
Xiangtao MengKevin J Edgar

Abstract

We describe the first synthesis of hydroxy-functionalized polysaccharide esters via chemoselective olefin hydroboration-oxidation in the presence of ester groups. Cellulose esters with terminally olefinic side chains were first synthesized by esterification of commercially available cellulose esters (e.g., cellulose acetate) with undec-10-enoyl chloride or pent-4-enoyl chloride. Subsequent two-step, one-pot hydroboration-oxidation reactions of the cellulose esters were performed, using 9-borabicyclo[3.3.1]nonane as hydroboration agent, followed by oxidizing the intermediate borane to a hydroxyl group using mildly alkaline H2O2. Sodium acetate was used as a weak base to catalyze the oxidation, thereby minimizing undesired ester hydrolysis. Characterization methods including FTIR, (1)H, and (13)C NMR proved the selectivity of the hydroboration-oxidation pathway, providing a family of novel cellulose ω-hydroxyalkanoyl esters that were previously difficult to access.

References

May 23, 2001·Advanced Drug Delivery Reviews·J Siepmann, N A Peppas
Aug 8, 2006·Journal of Pharmaceutical Sciences·Hajime Konno, Lynne S Taylor
Mar 9, 2011·Biomacromolecules·Nilanjana KarKevin J Edgar
Apr 13, 2013·Biomacromolecules·Xueyan ZhengKevin J Edgar
May 16, 2014·Journal of Pharmaceutical Sciences·Joyann A MarksKevin J Edgar

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Citations

Oct 8, 2016·Biomacromolecules·Laura I Mosquera-GiraldoLynne S Taylor
Jul 25, 2017·Carbohydrate Polymers·José A Heredia-GuerreroAthanassia Athanassiou

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