39967-60-7

Usage

Uses

Used in Research Applications:
2'-Deoxypseudouridine is used as a research chemical compound for studying the structure and function of nucleic acids, such as DNA and RNA. It can be employed in the development of new drugs and therapies targeting nucleic acid-related diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2'-Deoxypseudouridine is used as a key intermediate in the synthesis of various nucleoside-based drugs. These drugs have potential applications in the treatment of viral infections, cancer, and other diseases that involve nucleic acid metabolism.
Used in Diagnostic Applications:
2'-Deoxypseudouridine can also be used in the development of diagnostic tools and assays for detecting and monitoring diseases related to nucleic acid abnormalities. Its unique chemical properties make it a valuable component in the design of such diagnostic systems.

Upstream product

• 65236-74-0 O³,O⁵-dibenzyl-D-erythro-2-deoxy-pentose 
• 62880-74-4 5-lithio-2,4-di-t-butoxypyrimidine 
• 173327-56-5 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose 
• 1445-07-4 pseudouridine 
• 80545-50-2 3',5'-O-(tetraisopropyldisiloxanyl)-2'-O-<(imidazol-1-yl)thiocarbonyl>pseudouridine 
• 80545-49-9 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)pseudouridine 
• 1027202-34-1 5-[(2R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxymethyl-2,5-dihydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 130277-32-6 ((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2,3-dihydrofuran-2-yl)methanol 
• 664988-38-9 5-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-ribofuranosyl]-2,4-[bis(4-methoxybenzyloxy)]pyrimidine 
• 169526-37-8 (6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one 
• 22900-10-3 2-deoxy-D-ribose 
• 142189-87-5 2',3'-dideoxy-3'-oxopseudouridine 
• 80545-51-3 2'-deoxy-3',5'-O-(tetraisopropyldisiloxanyl)pseudouridine 

Downstream Products

• 65358-15-8 Pseudothymidine 
• 65358-17-0 5-(α-D-erythro-2-deoxy-pentofuranosyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 65358-16-9 1,3-Dimethyl-2'-deoxypseudouridine 
• 65358-18-1 2'-Deoxy-ψ-isocytidine 
• 289712-91-0 methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 3'-(2-cyanoethyl diisopropylphosphoramidite) 
• 289712-92-1 N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide 
• 289712-90-9 methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 
• 78064-58-1 3'-deoxy-1,3-dimethyl-ψ-uridine 

Relevant academic research and scientific papers

Total synthesis of pseudouridine: Via Heck-type C-glycosylation

The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

Conversion of 2-deoxy-D-ribose into 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine, 2′-deoxypseudouridine, and other C-(2′-deoxyribonucleosides)

The synthesis of 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine 2a, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-pyridine 23, 2-amino-5-(2-deoxy-β-D-ribofuranosyl)-3-methylpyridine 2b, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-3-methylpyridine 29 and 5-(2-deoxy-β-D-ribofuranosyl)-2,4-dioxopyrimidine [2′-deoxypseudouridine] 30a is described. These C-nucleosides are prepared either from 2-deoxy-3,5-O-(1, 1, 3, 3-tetraisopropyldisiloxan-1,3-diyl)-D-ribofuranose 15 or from 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-D-ribono-1,4-lactone 16, which are themselves prepared from 2-deoxy-D-ribose 13. The sugar derivatives are first allowed to react with the appropriate 5-lithio-pyridine or 5-lithio-pyrimidine derivatives, which are prepared from 5-bromo-2-(dibenzylamino)pyridine 12a, 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine 12b, 5-bromo-2-dibenzylamino-3-methylpyridine 25 and 5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine 33. The products from the reactions between the lithio-derivatives and the lactol 15 are cyclized under Mitsunobu conditions; the products from the reactions between the lithio-derivatives and the lactone 16 are first reduced with L-Selectride before cyclization, also under Mitsunobu conditions, In all cases, the β-anomers of the protected C-nucleosides are the predominant products. Finally, the separation of the α- and β-anomers and the removal of all of the protecting groups are described.

Nucleosides. 121. Improved and General Synthesis of 2'-Deoxy C-Nucleosides. Synthesis of 5-(2-Deoxy-β-D-erythro-pentofuranosyl)uracil, -1-methyluracil, -1,3-dimethyluracil, and -isocytosine

5-(2-Deoxy-β-D-erythro-pentofuranosyl)-1,3-dimethyluracil (6a), -1-methyluracil (6b), -uracil (6c), and -isocytosine (6d) were synthesized.Compounds 6b-d are C-nucleoside isosteres of thymidine, 2'-deoxyuridine, and 2'-deoxycytidine, respectively. 1,3-Dimethylpseudouridine (1a), 1-methylpseudouridine (1b), pseudouridine (1c), and pseudoisocytidine (1d) were treated with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane in pyridine to afford the corresponding 3',5'-tetraisopropyldisiloxanyl derivatives 2 which were converted into the respective 2'-O- C-nucleosides 3.Compounds 3a,b were converted directly into the corresponding 2'-deoxy β-C-nuleosides 5a,b exclusively by reduction with n-Bu3SnH.For the synthesis of 2'-deoxy β-C-nucleosides 5c,d, the intermediates 3c,d were trimethylsilylated prior to n-Bu3SnH treatment.Deprotection of 5a-d was effected by treatment with n-Bu4NF, and the corresponding free 2'-deoxy β-C-nucleosides 6a-d were obtained in good yields.

Pyrimidine to pyrimidine transformation process

There is provided a novel process for pyrimidine to pyrimidine transformations by the displacement of the 1,2,3-portion of a pyrimidine by a 1,3-ambident nucleophile. The novel process requires that the 1 and 3 nitrogens of the pyrimidine moiety be substituted. The novel process makes available, inter alia, novel uracils, simple methods of radioisotopically labeling pyrimidine nuclei, a simple and inexpensive method of preparing the important antiviral and antileukemic material pseudoisocytidine and its new active analog 2'-deoxypseudoisocytidine.