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A concise synthetic route from D-glucose to a chiral, biologically active, phosphorylated analogue of the highly potent Ca 2+ -mobilising agonist adenophostin A has been developed, involving a regioselective dibenzylation of allyl α-D-glucopyranoside and a one-pot Lemieux-type allyl oxidation with subsequent reduction and neighbouring deketalisation, to provide the key intermediate for phosphorylation.

Original publication

DOI

10.1039/C39950001169

Type

Journal article

Journal

Journal of the Chemical Society, Chemical Communications

Publication Date

01/12/1995

Pages

1169 - 1170