Deoxygenation of cis vicinal diols

Details Deoxygenation of cis vicinal diols Deoxygenation of cis vicinal diols

C - Chemistry, Metallurgy

07

H

C07H 19/06 (2006.01) C07C 1/32 (2006.01) C07C 15/58 (2006.01) C07C 67/317 (2006.01) C07C 67/327 (2006.01) C07C 69/58 (2006.01) C07D 405/04 (2006.01) C07D 473/00 (2006.01) C07F 7/10 (2006.01) C07H 19/16 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2154999

Cis vicinal diols are converted to olefins using tellurides or selenide reagents. The diol is reacted to convert the hydroxyl groups into good leaving groups for nucleophilic substitution. Alkyl and aryl sulfonate groups such as mesylate or tosylate are preferred. The product is then reacted with a source of Tc2- or Se2- ions, preferably an alkali metal telluride or selenide, to form the desired olefin. The process is particularly useful for generating 2',3'- unsaturation in the sugar moiety of nucleosides. Novel intermediate mesylate, tosylate and olefin derivatives of nucleosides are also provided.

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