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Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.

Shuai MengBishwa Raj BhetuwalPadam P AcharyaJianglong Zhu
Published in: Journal of carbohydrate chemistry (2019)
Synthesis of a variety of sugar lactols (hemiacetals) has been accomplished in moderate to excellent yields by using bromine-mediated oxidation of thioglycosides. It was found that acetonitrile is the optimal solvent for this oxidation reaction. This approach involving bromine as oxidant is superior to that using N-bromosuccimide (NBS) which produces byproduct succinimide often difficult to separate from the lactol products.
Keyphrases
  • hydrogen peroxide
  • electron transfer
  • visible light
  • nitric oxide