135197-63-6

Basic information

• Product Name: 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine
• Synonyms: 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine;3'-Deoxy-3'-fluoro-5'-O-tritylthymidine;3'-Deoxy-3'-fluoro-5'-O-(triphenylMethyl)thyMidine
• CAS NO: 135197-63-6
• Molecular Formula: C₂₉H₂₇FN₂O₄
• Molecular Weight: 486.54
• Product Categories: Aromatics;Bases & Related Reagents;Heterocycles;Nucleotides
• Mol File: 135197-63-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine(135197-63-6)
• EPA Substance Registry System: 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine(135197-63-6)

Safety Data

• Hazardous Substances Data: 135197-63-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine is used as an intermediate for the preparation of thymidine monophosphate analogues, which are essential in the development of antiviral and anticancer drugs. Its role in the synthesis process is crucial for creating effective therapeutic agents that target specific viral and cancer-related pathways.
As an intermediate, 3'-Deoxy-3'-fluoro-5'-O-trityl-D-thymidine contributes to the overall structure and function of the final thymidine monophosphate analogue, allowing for the creation of compounds with enhanced potency and selectivity against their respective targets. This makes it a valuable component in the ongoing efforts to develop new and improved treatments for various diseases.

Upstream product

• 50-89-5 thymidine 
• 141690-73-5 3'-Tosyl-5'-O-trityl thymidine 
• 76-83-5 trityl chloride 
• 7791-71-1 5'-O-tritylthymidine 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 16053-52-4 threothymidine 
• 101527-40-6 5'-O-tert-butyldiphenylsilylthymidine 
• 139212-95-6 5'-O-tert-butyldiphenylsilyl-3'-O-methanesulfonylthymidine 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 
• 104218-44-2 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 25442-42-6 5'-O-trityl-2,3'-anhydrothymidine 

Downstream Products

• 25520-83-6 phosphoric acid mono[3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahyrofuran-2-ylmethyl] ester 
• 699007-47-1 5-[bis(2,2,2-trifluoroethoxy)methyl]-3'-fluoro-5'-O-tert-butyldiphenylsilyl-2',3'-dideoxyuridine 
• 699007-45-9 5-(2,2,2-trifluoroethoxy)methyl-3'-fluoro-5'-O-tert-butyldiphenylsilyl-2',3'-dideoxyuridine 
• 136681-22-6 5-bromomethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-fluoro-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 116195-70-1 3'-fluoro-5'-O-tert-butyldiphenylsilyl-3'-deoxythymidine 
• 25526-93-6 alovudine 

Relevant articles and documents

Hydrofluorination of anhydrothymidine via soluble aluminum derivatives

A new method to stereospecifically hydrofluorinate anhydrothymidine has been discovered which allows the product to be obtained in higher yields than the current literature method.

Synthesis and Antiviral Activity of Novel Fluorinated 2′,3′ -Dideoxynucleosides

A series of 5-(trifluoroethoxymethyl)-2′,3′-dideoxyuridines and 5-[bis(trifluormethoxy)-methyl]-2′,3′-dideoxyuridines have been prepared and screened for antiviral activity. The conformations of these compounds are discussed on the bases of NOE studies and the MO calculations. Modelling and NOE studies suggest both syn- and anti conformations for these 5-(2,2,2-trifluoroethoxymethyl)- and 5-[bis(2,2,2-trifluoroethoxy)-methyl]-derivatives. The NOE parameters are also suggested to be more attributable to the nature of the fluorine atom than to structural or conformational changes. Compounds 17, 26 and 30 showed some activity in anti-HIV-1 and anti-HIV-2 assays, but the compounds were devoid of activity against HSV and human rhinovirus. The compounds tested exhibited low cytotoxicity and were inactive against a bank of cancer cells in vitro.

Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase

A number of 2′- and 3′-modified thymidine 5′-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2′-halogeno substituent and a 3′-azido function are the most favorable leads for further development of potent inhibitors of this enzyme.

Synthesis of 3'-fluoro-3'-deoxythymidine and studies of its 18F-radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drugs against AIDS

3'-Fluoro-3'-deoxy-thymidine (FDT), a fluorinated analog of 3'-azido-thymidine (AZT), is both more active against the HIV virus but also more toxic than AZT.Because of its fluorine atom, it can be labeled with 18F to be used to monitor this drug's biodistribution and targeting.A new synthesis for FDT, suited for 18F labeling, has been developed.After protecting the 5'-hydroxy group with a trityl group, the 3'-hydroxy group was substituted with a mesyl group in the lyxo configuration.Treatment with 18F potassium fluoride and crown-18 ether yielded the 18F-labeled fluoro derivative which on detritylation afforded 18F FDT with 7percent labeling efficiency.This is the first reported synthesis of 3'-fluoro-5'-O-trityl deoxythymidine using potassium fluoride and preparing its 18F labeled analog.The time required to incorporate 18F in the intermediate compound and isolate the end-product is reasonably short (approximately 2 h) which will allow sufficient time to conduct biological studies with this short-lived radionuclide.