1,3-Dimethyl-2'-deoxypseudoUridine

Compound 1,3-dimethyl-2'-deoxypseudoUridine is a C-nucleoside isomer of 1,3-dimethyl-2'-deoxyuridine. The 1,3-dimethyl-2'-deoxypseudoUridine can be synthesized from 1,3-dimethylpseudoUridine which can be obtained directly by treatment of pseudoUridine with dimethylformamide dimethyl acetal.

Catalog Number
65358-16-9
CAS
65358-16-9
Molecular Weight
256.26
Molecular Formula
C11H16N2O5

Chemical Information

Synonyms
(1R)-1,4-Anhydro-2-deoxy-1-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-erythro-pentitol; 5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione; 2,4(1H,3H)-Pyrimidinedione, 5-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3-dimethyl-
IUPAC Name
5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dimethylpyrimidine-2,4-dione
Canonical SMILES
CN1C=C(C(=O)N(C1=O)C)C2CC(C(O2)CO)O
InChI
InChI=1S/C11H16N2O5/c1-12-4-6(10(16)13(2)11(12)17)8-3-7(15)9(5-14)18-8/h4,7-9,14-15H,3,5H2,1-2H3/t7-,8+,9+/m0/s1
InChIKey
VUFZJLBBVTWRKA-DJLDLDEBSA-N
Boiling Point
457.7±55.0 °C at 760 mmHg
Purity
≥97%
Density
1.4±0.1 g/cm3
Storage
Storage at 2-8°C

Related Products

Synthesis of 1,3-dimethyl-2'-deoxypseudoUridine from 1,3-dimethylpseudoUridine

Compound 1,3-dimethyl-2'-deoxypseudoUridine is a C-nucleoside isomer of 1,3-dimethyl-2'-deoxyuridine. The 1,3-dimethyl-2'-deoxypseudoUridine can be synthesized from 1,3-dimethylpseudoUridine which can be obtained directly by treatment of pseudoUridine with dimethylformamide dimethyl acetal. C-nucleosides have attracted the attention of researchers since their discovery. Replacement of nucleobase nitrogen by carbon results in C-nucleosides which contain more stable C-C bond connected between ribose and base compared the C-N bond. C-nucleosides and their analogues present promising application for drug design. In recent years, C-nucleosides have shown great potential of the development of more effective and safer drugs.

A general method for producing 2'-deoxy C-nucleosides was developed. There were several 2'-deoxy C-nucleosides synthesized, including 1-methyl-2'-deoxypseudoUridine, 2'-deoxypseudoUridine and 2'-deoxypseudoisocytidine besides the 1,3-dimethyl-2'-deoxypseudoUridine. Take the example of the 1,3-dimethyl-2'-deoxypseudoUridine synthesis, the 3',5'-hydroxyl groups of C-nucleoside 1,3-dimethylpseudoUridine first were protected by treatment with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (TIPSCl) in pyridine to give the corresponding protected nucleoside in which only the 2'-hydroxyl group is available for modification. Following by the treatment with 1,1'-thiocarbonyldiimidazole (TCDI) in dimethylformamide to quantitatively convert into the 2'-O-thiocarbonyimidazole derivatives. Notably, under this condition, protected 1,3-dimethylpseudoUridine is treated with TCDI without the formation of by-products such as dinucleosidyl thiocarbonates. Removal of the silyl protecting group of 3',5'-hydroxyls with tetra-n-butylammonium fluoride (TBAF) in tetrahydrofuran caused the formation of the 2',3'-cyclic thiocarbonate. Thus, the step of deprotection has to be performed after reduction. Upon treatment of the 2'-O-thiocarbonyimidazole C-nucleoside with n-Bu3SnH, the TIPS protected 1,3-dimethyl-2'-deoxypseudoUridine was generated in good yields as the only isolable products. Due to the methylations of N1 and N3, the synthesis of 1,3-dimethyl-2'-deoxypseudoUridine do not need the procedures of protection and deprotection for amine. Finally, silyl protection (TIPS) of the C3' and C5' was removed by treatment with n-Bu4NF to afford the target product 1,3-dimethyl-2'-deoxypseudoUridine.

In conclusion, it has shown in literature that the C-nucleosides of biological interest were synthesized in good overall yields. The procedure for the synthesis of 2'-deoxy C-nucleosides described should have wide applicability in the C-nucleoside area.

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