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|Title:||Free radical substitutions of acyloxy groups in carbohydrate α-ketoesters|
|Citation:||Ferrier, R.J., Lee, C.-K., Wood, T.A. (1991). Free radical substitutions of acyloxy groups in carbohydrate α-ketoesters. Journal of the Chemical Society, Chemical Communications (10) : 690-691. ScholarBank@NUS Repository.|
|Abstract:||A range of carbohydrate derivatives containing α-ketoester functionality undergo efficient reductive loss of the acyloxy groups when treated with tri-n-butyltin hydride in refluxing benzene and in the presence of azoisobutyronitrile (AIBN) as radical initiator; under similar conditions, but with allyltri-n-butyltin instead of the hydride, efficient α-C-allylation takes place with axial substitution occurring preferentially in compounds with the ketoesters located within conformationally stable pyranoid rings; the methods represent novel ways of deoxygenating carbohydrate derivatives and of introducing branch points.|
|Source Title:||Journal of the Chemical Society, Chemical Communications|
|Appears in Collections:||Staff Publications|
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