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Synthesis and Molecular Structure of New Unsaturated Analogues of Nucleotides Containing Six‐Membered Rings
Author(s) -
Brel Valery K.,
Belsky Vitaly K.,
Stash Adam I.,
Zavodnik Valery E.,
Stang Peter J.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400523
Subject(s) - chemistry , moiety , nucleotide , stereochemistry , intramolecular force , pyrimidine , alkylation , purine , organic chemistry , catalysis , biochemistry , gene , enzyme
The reaction of 1‐(chloromethyl)‐3‐(diethoxyphosphonyl)allenes 15 and 16 with purine and pyrimidine bases in the presence of cesium carbonate afforded new acyclic analogs of nucleotides containing a 1,2‐alkadienic skeleton ( 17 − 24 ). Intramolecular cyclization of the alkoxides tethered to the allenyl moiety yielded dihydropyrans 33 − 38 and dihydrofurans 39 and 40 . Dealkylation of the dihydropyrans led to the corresponding phosphonic acids. The molecular structures of new nucleotide analogs 33 and 36 were determined by single‐crystal X‐ray analyses. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)