Reactions of closo-dodecaborate amines. Towards novel bis-(closo-dodecaborates) and closo-dodecaborate conjugates with lipids and non-natural nucleosides

• A series of bis-(closo-dodecaborate) species with amino linker were prepared.
• New closo-dodecaborate based lipid amides were synthesized.
• First conjugate of [B12H12]2− with 8-aza-7-deaza-2′-deoxyadenosine was obtained.

Alkylation, acylation and arylation reactions of closo-dodecaborate based amines were studied. First, bis-(closo-dodecaborate) species with terminal amino group tethered via linkers of different types were prepared by cleavage of cyclic oxonium adducts of closo-dodecaborate with closo-dodecaborate tertiary amines. Acylation of [B12H11OCH2CH2OCH2CH2N+H3]2− with fatty acid acyl chlorides afforded new closo-dodecaborate lipid amides. Reaction of [B12H11OCH2CH2OCH2CH2N+H3]2− with 4-chloro-1-(2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine followed by removal of protecting groups from the sugar residue resulted in the first conjugate of closo-dodecaborate with non-natural 8-aza-7-deaza-2′-deoxyadenosine nucleoside analog.

Alkylation, acylation and arylation reactions of closo-dodecaborate based amines were studied. Bis-(closo-dodecaborate) species with terminal amino group tethered via linkers of different types were prepared. First conjugate of closo-dodecaborate with non-natural 8-aza-7-deaza-2′-deoxyadenosine nucleoside analog was synthesized.Figure optionsDownload as PowerPoint slide