Purine nucleoside modifications by palladium catalyzed methods and compounds produced
First Claim
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1. A method for the preparation of a purine base, purine nucleoside or purine nucleotide modified at the 2-, 6- or 8-position of the purine ring 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.
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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
15 Claims
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1. A method for the preparation of a purine base, purine nucleoside or purine nucleotide modified at the 2-, 6- or 8-position of the purine ring 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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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11. A compound selected from the group consisting of:
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wherein Y is selected from the group consisting of —
C(O)R, —
COOR, —
C(O)NRR′
, —
CN, a substituted or unsubstituted aryl group or heterocyclic group, selected from the group consisting of phenyl, 2- , 3- or 4-hydroxyphenyl, 2-, 3- or 4-pyridyl and 1H-tetrazol-5-yl;
Z is selected from the group consisting of H, ribosyl, deoxyribosyl and dideoxyribosyl;
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. - View Dependent Claims (12, 13, 14, 15)
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Specification