• DOI:10.1016/j.carres.2014.03.005
Corpus ID: 30864604

An improved synthesis of 3,6-anhydro-D-glucal and a study of its unusual chemical reactivity.

@article{Basava2014AnIS,
  title={An improved synthesis of 3,6-anhydro-D-glucal and a study of its unusual chemical reactivity.},
  author={Vikram Basava and S. Gorun and Cecilia H Marzabadi},
  journal={Carbohydrate research},
  year={2014},
  volume={391},
  pages={
          106-11
        }
}

Vikram Basava, S. Gorun, Cecilia H Marzabadi

Published 2014

Chemistry, Medicine

Carbohydrate research

6-O-Tosyl-d-glucal 1 upon treatment with excess LiAlH4 unexpectedly gave 3,6-anhydro-d-glucal 2 as a major product in good yield. A crystal structure was obtained. Reaction of the anhydride 2 with N-iodosuccinimide (NIS) in excess methanol resulted in the formation of diastereomeric 2-deoxy-2-iodoglycosides. Addition of ceric (IV) ammonium nitrate and thiophenol to a solution of 2 in acetonitrile gave a mixture of 2-deoxy and 2,3-unsaturated thioglycosides. Reaction of 1,2:3,4-di-O… CONTINUE READING

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