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Issue 1, 2016
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Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

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Abstract

Hydroxybenzotriazole (HOBt) and HOBt-derived reagents have been classified as Class I explosives, with restrictions on their transportation and storage. We explored a range of benzoylated oxime-based reagents as alternatives to benzoyloxybenzotriazole (BBTZ) for the selective benzoylation of carbohydrate polyols. Benzoylated oximes derived from 2-hydroximino-malononitrile, ethyl 2-hydroximino-2-cyanoacetate (Oxyma), and tert-butyl 2-hydroximino-2-cyanoacetate were most effective for benzoylation of a simple primary alcohol, with yields approaching that obtained for BBTZ. When applied to carbohydrate diols, the most effective reagent was identified as benzoyl-Oxyma. Benzoyl-Oxyma is a highly crystalline, readily prepared alternative to BBTZ, useful in the selective benzoylation of carbohydrate polyols.

Graphical abstract: Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

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Publication details

The article was received on 09 Oct 2015, accepted on 28 Oct 2015 and first published on 29 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB02092A
Citation: Org. Biomol. Chem., 2016,14, 97-104
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    Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

    S. Burugupalli, S. Shah, P. L. van der Peet, S. Arora, J. M. White and S. J. Williams, Org. Biomol. Chem., 2016, 14, 97
    DOI: 10.1039/C5OB02092A

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