Supported Synthesis of Adenosine Nucleotides and Derivatives on a Benzene‐Centered Tripodal Soluble Support. Issue 21 (17th June 2021)

• Record Type: Journal Article
• Authors: Appy, Lucie; Peyrottes, Suzanne; Roy, Béatrice
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 21(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-06-17
• Subjects: Bisphosphonates -- Click reaction -- Nucleotides -- phosphorylation -- Soluble-supported synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100544
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The first soluble‐phase synthesis of adenosine nucleotides including α, β and β, γ ‐methylene bisphosphonate analogues on a multi‐pod support is reported. Anchoring of a 2', 3'‐protected purine nucleoside to the tripodal support via the nucleobase was successfully achieved using a microwave assisted Cu(I)‐catalyzed azide‐alkyne cycloaddition. Then, phosphorylation was performed, followed by cleavage with aqueous ammonia to provide adenine derivatives, and finally deprotection. When using benzylamine instead of ammonia, a derivative with N 6 ‐benzylamine adenine as nucleobase was obtained. This methodology allows to access adenosine 5'‐mono, di and triphosphates, as well as various analogues of pharmacological interest in modest to good yields. Abstract : A new strategy based on anchoring C(6) azidopurine nucleoside derivative to a tripodal soluble support allows to access the corresponding adenosine nucleotides. We extended the scope of the method to methylene bisphosphonate analogues and N 6 ‐benzylamine derivative.