Nucleoside modifications by palladium catalyzed methods
First Claim
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1. An oligonucleotide comprising a purine nucleoside modified at the 2-, 6- or 8-position of the purine ring prepared according to a method comprising comprising the steps of:
- reacting a purine starting material containing a leaving group attached to the 2-, 6- or 8-position of said purine starting material with a functionalized alkene having the formula;
whereinY is selected from the group consisting of —
CHROH, —
C(O)R, —
COOR, —
C(O)NRR′
, —
CN, a substituted or unsubstituted aryl group or heterocylic group, selected from the group consisting of phenyl, 2-,3- or 4-hydroxyphenyl, 2-,3- or 4-pyridyl and 1H-tetrazol-5-yl;
R and R′
are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl and aryl; and
n is an integer from 0-15 in the presence of a palladium catalyst of the general formula PdL3 or PdL4, wherein L is a ligand of palladium; and
isolating said modified nucleoside or nucleotide.
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Abstract
This invention discloses a method for the preparation of 2′-modified nucleosides, using a palladium catalyst and an alkene functionalized with a heteroatom. Included in the invention are the novel pyrimidines and purines that can be prepared according to the method of the invention and oligonucleotides containing said modified pyrimidines and purines.
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Citations
9 Claims
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1. An oligonucleotide comprising a purine nucleoside modified at the 2-, 6- or 8-position of the purine ring prepared according to a method comprising comprising the steps of:
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reacting a purine starting material containing a leaving group attached to the 2-, 6- or 8-position of said purine starting material with a functionalized alkene having the formula;
wherein Y is selected from the group consisting of —
CHROH, —
C(O)R, —
COOR, —
C(O)NRR′
, —
CN, a substituted or unsubstituted aryl group or heterocylic group, selected from the group consisting of phenyl, 2-,3- or 4-hydroxyphenyl, 2-,3- or 4-pyridyl and 1H-tetrazol-5-yl;
R and R′
are independently selected from the group consisting of H, substituted or unsubstituted alkyl, alkenyl and aryl; and
n is an integer from 0-15 in the presence of a palladium catalyst of the general formula PdL3 or PdL4, wherein L is a ligand of palladium; and
isolating said modified nucleoside or nucleotide. - View Dependent Claims (2, 3)
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4. An oligonucleotide comprising a pyrimidine nucleoside modified at the 5-or 6-position of the pyrimidine ring prepared according to a method comprising the steps of:
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reacting a pyrimidine starting material containing a leaving group attached to the 5- or 6-position of said pyrimidine starting material with a functionalized alkene having the formula;
wherein Y is selected from the group consisting of —
C(O)R, —
COOR, —
C(O)NRR′
, —
CN, phenyl, 2-, 2- or 4- hydroxyphenyl, 2-,3- or 4-pyridyl and 1H-tetrazol-5-yl;
R and R′
are independently selected from the group consisting of H, alkyl, alkenyl and aryl; and
n is an integer from 1-15 in the presence of a palladium catalyst of the general formula PdL3 or PdL4, wherein L is a ligand of palladium to produce a pyrimidine nucleoside having the following formula;
wherein Z is selected from the group consisting of H, ribose, deoxyribose, dideoxyribose and derivatives thereof; and
isolating said modified nucleoside. - View Dependent Claims (5, 6)
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7. An oligonucleotide comprising a pyrimidine nucleoside modified at the 5-or 6-position of the pyrimidine ring prepared according to a method comprising the steps of:
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reacting a pyrimidine starting material containing a leaving group attached to the 5- or 6-position of said pyrimidine starting material with a functionalized alkene having the formula;
wherein Y is CHROH;
R is independently selected from the group consisting of H, alkyl, alkenyl and aryl; and
n is an integer from 0-15 in the presence of a palladium catalyst of the general formula PdL3 or PdL4, wherein L is a ligand of palladium to produce a pyrimidine nucleoside having the following formula;
wherein Z is selected from the group consisting of H, ribose, deoxyribose, dideoxyribose and derivatives thereof; and
isolating said modified nucleoside. - View Dependent Claims (8, 9)
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Specification