Synthesis of spirocyclic glucose-proline hybrids and methods...

Details Synthesis of spirocyclic glucose-proline hybrids and methods... Synthesis of spirocyclic glucose-proline hybrids and methods...

C - Chemistry, Metallurgy

07

H

C07H 99/00 (2006.01) C07K 1/107 (2006.01) C07D 491/107 (2006.01)

Patent

CA 2568954

A short synthetic route to polyhydroxylated spirocyclic glucose-based L- proline analogues is described from easily prepared 2,3,4,6 tetra-O-benzyl-D- glucono- lactone. The synthesis involves C-glycosylation of an exocyclic glucose-based epoxide with allyltributylstannane that affords functionalized C-ketosides containing a .alpha.-hydroxy ester moiety. Oxidation of the alcohol function, followed by stereoselective reductive amination provides an amine that undergoes iodine-induced aminocyclization to provide spirocyclic glucose-proline hybrids bearing an iodomethylene side-chain. The iodo function of the side-chain can be converted into other functional groups such as ester- and hydroxyl group thereby allowing additional modifications to the pyrrolidine ring. Deprotection of the sugar scaffold produces spirocyclic glucose proline hybrids that can be converted into polyfunctional amino-protected acids that serve as building blocks in peptide synthesis.

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