104766-16-7

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine
• Synonyms: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine
• CAS NO: 104766-16-7
• Molecular Weight: 544.604
• Mol File: 104766-16-7.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine(104766-16-7)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-α-thymidine(104766-16-7)

Safety Data

• Hazardous Substances Data: 104766-16-7(Hazardous Substances Data)

Upstream product

• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 4784-41-2 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine 
• 4449-43-8 α-deoxythymidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 50-89-5 thymidine 
• 115393-52-7 5'-O-dimethoxytritylthymidine-3'-O-β-cyanoethoxymethylphosphonite 
• 114079-04-8 5'-dimethoxytritylthymidine-3'-diisopropylaminomethylphosphonoamidite 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 15981-92-7 2,3'-anhydrothymidine 
• 220928-58-5 5'-O-(4,4'-dimethoxytrityl)-3'-C-(benzoyl)thymidine 
• 220928-53-0 1-(5-O-(4,4'-dimethoxytrityl)-3-C-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)thymine 
• 220928-57-4 5'-O-(4,4'-dimethoxytrityl)-3'-C-(2,2-dimethylpropanoyl)thymidine 
• 220928-52-9 1-(5-O-(4,4'-dimethoxytrityl)-3-C-(1,1-dimethylpropanoyl)-2-deoxy-β-D-threo-pentofuranosyl)thymine 

Downstream Products

• 25526-93-6 alovudine 
• 116003-06-6 C₄₀H₄₉N₄O₈P 
• 156056-16-5 5'-O-dimethyoxytrityl-3'-O-(tert-butyldimethylsilyl)-N-4-benzoyl-5-methyl-2'-deoxy-α-cytidine 
• 152581-55-0 5'-O-dimethoxytrityl-3'-O-(tert-butyldimethylsilyl)-5-methyl-2'-deoxy-α-cytidine 
• 219706-33-9 3'-O-(2-cyanoethyldiisopropylphosphoramidite)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-N⁴-(1-pyrenylmethyl)-α-cytidine 
• 219706-29-3 Acetic acid (2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-{5-methyl-2-oxo-4-[(pyren-1-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl ester 
• 219706-31-7 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-N⁴-(1-pyrenylmethyl)-α-cytidine 
• 219706-39-5 3'-O-acetyl-N⁴-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-α-cytidine 
• 219706-26-0 1-<3'-O-acetyl-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl>-5-methyl-4-(1,2,4-triazolyl)pyrimidine-2(1H)-one 
• 219706-37-3 3'-O-acetyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-α-cytidine 
• 152601-85-9 N⁴-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-5-methyl-α-cytidine 
• 149666-71-7 1-{5-[bis(4-methoxyphenyl)phenyl-methoxymethyl]-2,5-dihydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 290371-78-7 5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine 
• 1150314-64-9 C₃₆H₃₈N₂O₉ 

Relevant articles and documents

Synthesis of Thymidine Dimers Containing Piperazine in the Internucleoside Linkage and their Incorporation into Oligodeoxynucleotides

The synthesis of thymidine dimers in which the natural phosphodiester linkage has been replaced by piperazine (3'-(N(CH2CH2)2N)-5, 9 and 3'-(N(CH2CH2)2N)-CO-4, 10) are described.These new dimers were incorporated into oligodeoxynucleotides on an automated DNA-synthesizer using the phosphoramidite approach.The thermal stability of DNA/DNA duplexes and the enzymatic stability was studied by UV experiments. 17-Mers with 9 incorporated once or twice in the middle exhibited a pronounced decrease in thermal stability (ΔTm -11 degC per modification) while 17-mers with 10 incorporated once or twice in the middle exhibited only a slight decrease in thermal stability (ΔTm -2 degC per modification) when compared to unmodified 17-mers.Furthermore, end-modified oligodeoxynucleotides containing either 9 or 10 displayed five to six fold increased stability towards snake venom phosphodiesterase.

Synthesis and evaluation of 3′-[18F]fluorothymidine-5′-squaryl as a bioisostere of 3′-[18F]fluorothymidine-5′-monophosphate

The squaryl moiety has emerged as an important phosphate bioisostere with reportedly greater cell permeability. It has been used in the synthesis of several therapeutic drug molecules including nucleoside and nucleotide analogues but is yet to be evaluated in the context of positron emission tomography (PET) imaging. We have designed, synthesised and evaluated 3′-[18F]fluorothymidine-5′-squaryl ([18F]SqFLT) as a bioisostere to 3′-[18F]fluorothymidine-5′-monophosphate ([18F]FLTMP) for imaging thymidylate kinase (TMPK) activity. The overall radiochemical yield (RCY) was 6.7 ± 2.5% and radiochemical purity (RCP) was >90%. Biological evaluationin vitroshowed low tracer uptake (?1) but significantly discriminated between wildtype HCT116 and CRISPR/Cas9 generated TMPK knockdown HCT116shTMPK?. Evaluation of [18F]SqFLT in HCT116 and HCT116shTMPK?xenograft mouse models showed statistically significant differences in tumour uptake, but lacked an effective tissue retention mechanism, making the radiotracer in its current form unsuitable for PET imaging of proliferation.

Radiolabeled cyclosaligenyl monophosphates of 5-iodo-2′-deoxyuridine, 5-iodo-3′-fluoro-2′,3′-dideoxyuridine, and 3′-fluorothymidine for molecular radiotherapy of cancer: Synthesis and biological evaluation

Targeted molecular radiotherapy opens unprecedented opportunities to eradicate cancer cells with minimal irradiation of normal tissues. Described in this study are radioactive cyclosaligenyl monophosphates designed to deliver lethal doses of radiation to cancer cells. These compounds can be radiolabeled with SPECT- and PET-compatible radionuclides as well as radionuclides suitable for Auger electron therapies. This characteristic provides an avenue for the personalized and comprehensive treatment strategy that comprises diagnostic imaging to identify sites of disease, followed by the targeted molecular radiotherapy based on the imaging results. The developed radiosynthetic methods produce no-carrier-added products with high radiochemical yield and purity. The interaction of these compounds with their target, butyrylcholinesterase, depends on the stereochemistry around the P atom. IC50 values are in the nanomolar range. In vitro studies indicate that radiation doses delivered to the cell nucleus are sufficient to kill cells of several difficult to treat malignancies including glioblastoma and ovarian and colorectal cancers.