173097-87-5Relevant academic research and scientific papers
Efficient synthesis of α-branched purine-based acyclic nucleosides: Scopes and limitations of the method
Dra?ínsky, Martin,Frydrych, Jan,Janeba, Zlatko,Slavětínská, Lenka Po?tová
, (2020)
An efficient route to acylated acyclic nucleosides containing a branched hemiaminal ether moiety is reported via three-component alkylation of N-heterocycle (purine nucleobase) with acetal (cyclic or acyclic, variously branched) and anhydride (preferentially acetic anhydride). The procedure employs cheap and easily available acetals, acetic anhydride, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The multi-component reaction is carried out in acetonitrile at room temperature for 15 min and provides moderate to high yields (up to 88%) of diverse acyclonucleosides branched at the aliphatic side chain. The procedure exhibits a broad substrate scope of N-heterocycles and acetals, and, in the case of purine derivatives, also excellent regioselectivity, giving almost exclusively N-9 isomers.
Nucleotides. Part XLV. Synthesis of new (2'-5')adenylate trimers, containing 5'-amino-5'-deoxyadenosine residues at the 5'-end of the oligoadenylate chain, and of its analogues, carrying a 9-[(2-hydroxyethoxy)methyl]adenine residue at the 2'-terminus
Kvasyuk,Kulak,Mikhailopulo,Charubala,Pfleiderer
, p. 1777 - 1784 (2007/10/02)
The 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (4) was obtained in pure form from 2',3'-O-isopropylideneadenosine (1), without isolation of intermediates 2 and 3. The 2-(4-nitrophenyl)ethoxycarbonyl group was used for protection of the NH2 functions of 4 (→ 7). The selective introduction of the palmitoyl (= hexadecanoyl) group into the 5'-N-position of 4 was achieved by its treatment with palmitoyl chloride in MeCN in the presence of Et3N (→ 5). The 3'-O-silyl derivatives 11 and 14 were isolated by column chromatography after treatment of the 2',3'-O-deprotected compounds 8 and 9, respectively, with (tert-butyl)dimethylsilyl chloride and 1H-imidazole in pyridine. The corresponding phosphoramidites 16 and 17 were synthesized from nucleosides 11 and 14, respectively, and (cyanoethoxy)bis(diisopropylamino)phosphane in CH2Cl2. The trimeric (2'-5')-linked adenylates 25 and 26 having the 5'-amino-5'-deoxyadenosine and 5'-deoxy-5'-(palmitoylamino)adenosine residue, respectively, at the 5'-end were prepared by the phosphoramidite method. Similarly, the corresponding 5'-amino derivatives 27 and 28 carrying the 9-[(2-hydroxyethoxy)methyl]adenine residue at the 2'-terminus, were obtained. The newly synthesized compounds were characterized by physical means. The synthesized trimers 25-28 were 3-, 15-, 25-, and 34-fold, respectively, more stable towards phosphodiesterase from Crotalus durissus than the trimer (2'-5')ApApA.
