161110-05-0

Basic information

• Product Name: 3'-Deoxy-5'-O-trityl-D-uridine
• Synonyms: 3'-Deoxy-5'-O-trityl-D-uridine;3'-Deoxy-5'-O-(triphenylMethyl)uridine
• CAS NO: 161110-05-0
• Molecular Formula: C28H26N2O5
• Molecular Weight: 470.522
• Product Categories: Bases & Related Reagents;Nucleotides;Nucleotides, Bases & Related Reagents
• Mol File: 161110-05-0.mol

Chemical Properties

• Melting Point: 82-88°C
• Appearance: /
• CAS DataBase Reference: 3'-Deoxy-5'-O-trityl-D-uridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Deoxy-5'-O-trityl-D-uridine(161110-05-0)
• EPA Substance Registry System: 3'-Deoxy-5'-O-trityl-D-uridine(161110-05-0)

Safety Data

• Hazardous Substances Data: 161110-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
3'-Deoxy-5'-O-trityl-D-uridine is used as a protected intermediate for the synthesis of various nucleoside analogs, which are essential in the development of new anti-cancer and anti-viral drugs. The trityl group protects the molecule from unwanted reactions, allowing for selective functionalization and modification of the uridine moiety.
Used in Biochemical Studies:
In the field of biochemistry, 3'-Deoxy-5'-O-trityl-D-uridine is used as a labeled compound for studying the interactions of nucleosides with enzymes, receptors, and other biomolecules. The trityl group can be used as a chromophore for monitoring the progress of enzymatic reactions or as a handle for immobilizing the molecule on solid supports for affinity chromatography and other separation techniques.
Used in Chemical Synthesis:
3'-Deoxy-5'-O-trityl-D-uridine serves as a key building block in the chemical synthesis of complex nucleoside derivatives and modified oligonucleotides. The trityl group provides stability during the synthesis process, allowing for the introduction of various functional groups and modifications to the uridine moiety without compromising the integrity of the molecule.
Used in Antiviral Applications:
3'-Deoxy-5'-O-trityl-D-uridine is used as a potential anti-viral agent, particularly against RNA and DNA viruses. The molecule can be further modified to target specific viral enzymes or receptors, inhibiting viral replication and reducing the spread of the virus within the host.
Used in Cancer Therapy:
In cancer therapy, 3'-Deoxy-5'-O-trityl-D-uridine is used as a potential anti-cancer agent. The molecule can be modified to target specific cancer cell markers or enzymes, leading to the inhibition of cancer cell growth and proliferation. Additionally, the molecule can be used in combination with other chemotherapeutic agents to enhance their efficacy and overcome drug resistance in cancer cells.

Upstream product

• 130860-05-8 2,2'-anhydro-1-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 3249-94-3 5′-O-trityl-2,2′-anhydro-β-D-uridine 
• 76-83-5 trityl chloride 
• 130860-04-7 2,2'-anhydro-1-<3-O-(phenoxythiocarbonyl)-5-O-trityl-β-D-threo-pentofuranosyl>uracil 
• 6554-10-5 5'-O-trityluridine 
• 58-96-8 uridine 
• 130860-12-7 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-5'-O-trityluridine 
• 117136-35-3 2'-O-(tert-butyldimethylsilyl)-5'-O-(triphenylmethyl)uridine 
• 130860-11-6 2'-O-(tert-butyldimethylsilyl)-3'-O-(phenoxythiocarbonyl)-5'-O-trityluridine 
• 161109-82-6 2'-O-thexyldimethylsilyl-5'-O-trityluridine 
• 161109-93-9 3'-O-phenoxythiocarbonyl-2'-O-thexyldimethylsilyl-5'-O-trityluridine 

Downstream Products

• 7057-27-4 3'-deoxyuridine 
• 7057-33-2 3'-deoxycytidine 

Relevant articles and documents

Nucleosides. LVI. Synthesis and chemical modifications of 3'-deoxy- pyrimidine nucleosides

3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O- toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert- butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterized by elemental analyses and UV and 1H-NMR spectra.

Synthesis and Anticancer Activity of Various 3'-Deoxy Pyrimidine Nucleoside Analogues and Crystal Structure of 1-(3-Deoxy-β-D-threo-pentofuranosyl)cytosine

Various 3'-deoxy pyrimidine nucleoside analogues have been synthesized for evaluation as potential anticancer and antiviral agents.Among these compounds, 1-(3-deoxy-β-D-threo-pentofuranosyl)cytosine (10, 3'-deoxy-ara-C) and 3'-deoxycytidine (22) had significant anticancer activity against CCRF-CEM, L1210, P388, and S-180 cancer cell lines in vitro, producing ED50 values of 2,10,5,and 34 μM, respectively, for 3'-deoxy-ara-C (10); and 25, 5, 2.5, and 15μM, respectively, for 3'-deoxycytidine (22).Thus, 3'-deoxy-ara-C (10) was 12.5 times more active against CCRF-CEM cells than 3'-deoxycytidine (22).The 2'-O-acetyl, 5'-O-acetyl, and 2',5'-di-O-acetyl derivatives of 3'-derivatives of 3'-deoxy-ara-C (10), compounds 34, 31, and 30, demonstrated anticancer activity in the same range as 3'-deoxy-ara-C (10) against CCRF-CEM, L1210, P388, and S-180 cells.The 5'-O-acetyl derivative (31) had significantly greater activity against CCRF-CEM with an ED50 value of 0.4 but this compound also showed similar activity, as did 3'-deoxy-ara-C against L1210, P388, and S-180 with ED50 values of 3, 3, and 13 μM, respectively. 3'-Deoxy-ara-C was also evaluated in vitro against HSV-2, HCMV, and GPCMV viruses and was found to be not very active with respective IC50 values of 110, 220, and 1000 μM.The single-crystal structure of 3'-deoxy-ara-C (10) was determined by X-ray crystallography.There are two molecules of the nucleoside and one molecule of water in the asymmetric unit.The sugar moieties of two nucleoside molecules adopt different conformations.In molecule A, the ring pucker is C3'-endo with P=18.7 deg and τm= 37.3 deg, while the CH2OH side chain is gauche+.In molecule B, the ring pucker is C2'-endo with P= 156.8 deg and τm = 37.8 deg and the side chain is trans.