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Improved Synthesis of the C-Glucuronide/Glycoside of 4-Hydroxybenzylretinone (4-HBR).

Kathryn R CavanaughSureshbabu NarayanasamyJoel R WalkerMargaret Clagett-DameRobert W Curley
Published in: Journal of carbohydrate chemistry (2016)
Improvements in the synthesis of carbon-linked glucuronide/glucoside conjugates of cancer chemopreventive retinoids have been achieved starting with 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The revised approach demonstrates better yields, eliminates the use of an expensive, carcinogenic protecting group reagent, and avoids much painstaking chromatography. The new approach should allow synthesis of larger quantities of the agents for detailed animal and mechanistic studies.
Keyphrases
  • mass spectrometry
  • papillary thyroid
  • high performance liquid chromatography
  • drug delivery
  • tandem mass spectrometry
  • cancer therapy
  • liquid chromatography