title: Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent.
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.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria, Australia 3010. sjwill@unimelb.edu.au.
authors.forename: Satvika
authors.initials: S
authors.lastname: Burugupalli
authors.forename: Sayali
authors.initials: S
authors.lastname: Shah
authors.forename: Phillip L
authors.initials: PL
authors.lastname: van der Peet
authors.forename: Seep
authors.initials: S
authors.lastname: Arora
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: Spencer J
authors.initials: SJ
authors.lastname: Williams
mesh_terms: D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D011245:Pregnadienes / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry
chemical_list: C430943:1-(benzoyloxy)benzotriazole; D007202:Indicators and Reagents; D010091:Oximes; D011245:Pregnadienes; D014230:Triazoles; C045419:oxyma