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

作者：Basava Vikram; Gorun Sergiu M; Marzabadi Cecilia H^*

来源：Carbohydrate Research, 2014, 391: 106-111.

DOI：10.1016/j.carres.2014.03.005

• 3, 6-Anhydro-D-glucal
• 6-O-Tosyl-D-glucal
• Addition reactions
• Dianhydride sugar

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-alpha-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.

• 出版日期2014-6-4