The 7-oxabicyclo[2.2.1]heptanyl system provides a rapid entry to carbohydrate derivatives in a stereoselective manner by virtue of the rigid framework. The formation of this bicyclic system through a Diels-Alder reaction of furan with a number of dienophiles is influenced by the substitution on the dienophile. Use of an anion stabilising group as a carbonyl equivalent has previously led to a ring opening reaction of the bicyclic system. However, anion chemistry can be used to functionalise the bicyclic system, and used for the introduction of a hydroxy group that allows, in turn, a method for the preparation of hexose derivatives

The 7-oxabicyclo[2.2.1]heptanyl system allows rapid and stereoselective preparation of carbohydrate derivatives, including hexose derivatives, through a Diels-Alder reaction with furan and dienophiles.

Paper

Development of methodology based on the use of the 7-oxabicyclo[2.2.1]heptanyl system for the preparation of carbohydrate derivatives

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