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Microwave-assisted Synthesis Of 2'-O-aryluridine Derivatives.

Yusuke Oeda, Yoshihiro Iijima, H. Taguchi, A. Ohkubo, K. Seio, M. Sekine
Published 2009 · Chemistry, Medicine

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A new method for the synthesis of 2'-O-aryluridines was developed via the microwave-mediated reaction of 2,2'-anhydrouridine with aromatic alcohols. Aminophenol and aminonaphthol derivatives underwent selective 2'-O-arylation with 2,2'-anhydrouridine to produce 2'-O-(aminoaryl)uridine derivatives. These reactions proved to proceed without the need for any bases or solvents, but better results were obtained by use of N,N-dimethylacetamide (DMA) as the solvent in some cases.
This paper references
10.1016/J.TET.2008.02.075
Synthesis and hybridization properties of 2′-O-(tetrazol-5-yl)ethyl-modified oligonucleotides
H. Saneyoshi (2008)
10.1517/17425247.2.1.3
Modulation of gene expression by antisense and antigene oligodeoxynucleotides and small interfering RNA
R. Mahato (2005)
10.1351/pac199971081417
Approaches to catalyst discovery. New carbon–heteroatom and carbon–carbon bond formation
J. Hartwig (1999)
10.1016/j.drudis.2008.05.007
Chemically modified siRNA: tools and applications.
J. K. Watts (2008)
10.1016/J.TET.2008.04.110
Phosphoramidite building blocks for efficient incorporation of 2′-O-aminoethoxy(and propoxy)methyl nucleosides into oligonucleotides
G. V. Bobkov (2008)
10.1039/B000114G
Bicyclic nucleosides and conformational restriction of oligonucleotides
M. Meldgaard (2000)
10.1016/S0167-7799(02)00038-0
LNA: a versatile tool for therapeutics and genomics.
M. Petersen (2003)
10.1016/J.CBPA.2004.10.007
RNA interference and chemically modified small interfering RNAs.
M. Manoharan (2004)
SECOND GENERATION OF ANTISENSE OLIGONUCLEOTIDES : FROM NUCLEASE RESISTANCETO BIOLOGICAL EFFICACY IN ANIMALS
K. Altmann (1996)
10.1021/JO051741R
A general method for the synthesis of 2'-O-cyanoethylated oligoribonucleotides having promising hybridization affinity for DNA and RNA and enhanced nuclease resistance.
H. Saneyoshi (2005)
10.1021/JA00096A059
Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes
A. Guram (1994)
10.5059/YUKIGOSEIKYOKAISHI.57.969
Syntheses and Properties of Novel Conformationally Restrained Nucleoside Analogues
T. Imanishi (1999)
10.1016/j.bmc.2008.11.042
Synthesis of oligodeoxynucleotides incorporating 2-N-carbamoylguanine and evaluation of the hybridization properties.
Takeshi Sasami (2009)
10.1021/JM950937O
2'-O-aminopropyl ribonucleotides: a zwitterionic modification that enhances the exonuclease resistance and biological activity of antisense oligonucleotides.
R. Griffey (1996)
10.1248/CPB.52.1399
Development of bridged nucleic acid analogues for antigene technology.
S. Obika (2004)
10.1021/jm701537z
Comparing in vitro and in vivo activity of 2'-O-[2-(methylamino)-2-oxoethyl]- and 2'-O-methoxyethyl-modified antisense oligonucleotides.
T. P. Prakash (2008)
10.1093/OXFORDJOURNALS.JBCHEM.A127892
SPECIFIC MODIFICATION OF NUCLEIC ACIDS AND THEIR CONSTITUENTS WITH TRINITROPHENYL GROUP.
M. Azegami (1964)
10.1135/CCCC20060804
Synthesis of Oligoribonucleotides Containing Pyrimidine 2'- O -[(Hydroxyalkoxy)methyl]ribonucleosides
G. V. Bobkov (2006)
10.1016/J.TET.2007.07.102
Chemical synthesis of RNA via 2′-O-cyanoethylated intermediates
H. Saneyoshi (2007)
10.1016/S0040-4020(98)00271-3
2′-O-Propargyl oligoribonucleotides: Synthesis and hybridisation
M. Grøtli (1998)
10.1016/J.BMC.2007.09.019
Synthesis of 2'-O-modified adenosine building blocks and application for RNA interference.
D. Odadzic (2008)
10.1021/JA044637K
Structural rationalization of a large difference in RNA affinity despite a small difference in chemistry between two 2'-O-modified nucleic acid analogues.
R. Pattanayek (2004)
10.1021/OL034561H
An air and thermally stable one- component catalyst for the amination of aryl chlorides.
D. Zim (2003)
10.1021/JO00034A031
Nucleic acid related compounds. 73. Fluorination of uridine 2'-thioethers with xenon difluoride or (diethylamino)sulfur trifluoride. Synthesis of stable 2'-[alkyl(or aryl)sulfonyl]-2'-deoxy-2'-fluorouridines
M. J. Robins (1992)
10.1089/108729002760070849
Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action.
M. Manoharan (2002)
10.1172/JCI33483
Chemical modification: the key to clinical application of RNA interference?
D. Corey (2007)
10.1021/jo01310a027
Meisenheimer spiro picryl complex of adenosine. Example of a stereoselective dioxolane ring opening in an acidic medium
Guy Ah-Kow (1980)
10.1089/1545457041526326
Poly-2'-DNP-RNAs with enhanced efficacy for inhibiting cancer cell growth.
X. Chen (2004)
10.1039/P19820001625
Reaction between 2,2′-anhydro-1-β-D-arabinofuranosyluracil and thiolate ions
K. J. Divakar (1982)
10.1021/JA00092A058
Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides
F. Paul (1994)
10.1021/jo800451m
Preparation of zwitterionic ribonucleoside phosphoramidites for solid-phase siRNA synthesis.
Romualdas Smicius (2008)
10.1038/nchembio839
RNAi therapeutics: a potential new class of pharmaceutical drugs
D. Bumcrot (2006)
10.1016/S0167-4781(99)00138-4
2'-carbohydrate modifications in antisense oligonucleotide therapy: importance of conformation, configuration and conjugation.
M. Manoharan (1999)
10.1021/AR980051P
Synthesis of 3‘-C- and 4‘-C-Branched Oligodeoxynucleotides and the Development of Locked Nucleic Acid (LNA)
J. Wengel (1999)
10.1021/BI00081A031
Oligodeoxynucleotides containing 2'-O-modified adenosine: synthesis and effects on stability of DNA:RNA duplexes.
E. Lesnik (1993)
10.1021/OL049470E
2'-O-[2-(guanidinium)ethyl]-modified oligonucleotides: stabilizing effect on duplex and triplex structures.
T. P. Prakash (2004)



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