BIOMAT Database Logo BIOMAT Database Logo

Synthesis of cyclobutane nucleosides. 2011

Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Department of Chemistry, York University, Toronto, Ontario, Canada.

2-(6-Chloropurinyl)-3-benzoyloxymethylcyclobutanone can be prepared by reaction of 6-chloropurine with 3-benzoyloxymethyl-2-bromocyclobutanone. The N-alkylation gave both N-9 and N-7 regioisomers. Both regioisomers upon hydride reduction followed by aminolysis gave the corresponding adenine nucleoside analogues. However, the N-7 series led to the hypoxanthine analogues as byproducts.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D009705 Nucleosides Purine or pyrimidine bases attached to a ribose or deoxyribose. (From King & Stansfield, A Dictionary of Genetics, 4th ed) Nucleoside,Nucleoside Analog,Nucleoside Analogs,Analog, Nucleoside,Analogs, Nucleoside
D003503 Cyclobutanes Four carbon cycloparaffin cyclobutane (the structural formula (CH2)4) and its derivatives.
D000225 Adenine A purine base and a fundamental unit of ADENINE NUCLEOTIDES. Vitamin B 4,4, Vitamin B,B 4, Vitamin
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations

Related Publications

Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis and conformational analysis of new cyclobutane-fused nucleosides.
February 2006, Organic letters,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis of cyclobutane nucleosides 2-preparation of thymine and uracil analogues.
January 2015, Nucleosides, nucleotides & nucleic acids,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis, anti-HIV activity studies, and in silico rationalization of cyclobutane-fused nucleosides.
June 2012, ChemMedChem,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis and antiviral and cytostatic activities of carbocyclic nucleosides incorporating a modified cyclobutane ring. Part 1: Guanosine analogues.
October 1999, Archiv der Pharmazie,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis of cyclobutane serine analogues.
January 2005, The Journal of organic chemistry,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
[Synthesis of novel nucleosides: carbocyclic nucleosides].
July 1995, Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Nucleosides. LXV. Synthesis of new pteridine-N8-nucleosides.
January 2004, Nucleosides, nucleotides & nucleic acids,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Supramolecular photochemical synthesis of an unsymmetrical cyclobutane.
October 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
SYNTHESIS OF AMINOSUGAR NUCLEOSIDES.
November 1962, Journal of medicinal and pharmaceutical chemistry,
Abdelaziz Ebead, and Rene Fournier, and Edward Lee-Ruff
Synthesis of fluorinated nucleosides.
July 2006, Current protocols in nucleic acid chemistry,
Copied contents to your clipboard!