Article
An Improved Synthesis of 3,6-anhydro-d-glucal and a Study of its Unusual Chemical Reactivity
Carbohydrate Research
(2014)
Abstract
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-isopropylidine-α-d-galactopyranose with the anhydro sugar 2 in the presence of N-iodosuccinimide did not give the expected iodoglycoside mixture, but instead gave an unusual 1,4:3,6-dianhydride 7 as the major product.
Keywords
- 3 6-Anhydro-d-glucal,
- 6-O-Tosyl-d-glucal,
- Addition reactions,
- Dianhydride sugar
Disciplines
Publication Date
June 4, 2014
DOI
10.1016/j.carres.2014.03.005
Citation Information
Sergiu M. Gorun, Vikram Basava and Cecilia H. Marzabadi. "An Improved Synthesis of 3,6-anhydro-d-glucal and a Study of its Unusual Chemical Reactivity" Carbohydrate Research Vol. 391 (2014) p. 106 - 111 Available at: http://works.bepress.com/sergiu_gorun/5/