Some synthetic routes to 2,3,6-trideoxy-hex-2-enopyranosides and -hex-2-enopyranosid-4-uloses

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Abstract
Routes to 6-deoxy-hex-2-enopyranosides and the corresponding 4-ulo derivatives have been investigated. The route (Scheme 2) beginning with the readily prepared ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside is preferred, and the steps involve selective tosylation, iodinolysis, and reduction with Raney nickel. During the iodinolysis step a rearrangement occurs leading to furan derivatives. However, tliis is suppressed completely by the addition of pyridine to the iodinolysis medium. If the 4-ulo derivative is the desired substance, the most direct route (Scheme 3) utilises the well-known 2,3-dideoxy-hex-2-enopyranosid-4-ulose, the primary hydroxyl group being removed in two simple steps.