35898-29-4

Basic information

• Product Name: Thymidine, 5'-benzoate
• Synonyms: 5'-O-Benzoylthymidine;Thymidine,5'-benzoate
• CAS NO: 35898-29-4
• Molecular Formula: C17H18N2O6
• Molecular Weight: 346.34
• Mol File: 35898-29-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Thymidine, 5'-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5'-benzoate(35898-29-4)
• EPA Substance Registry System: Thymidine, 5'-benzoate(35898-29-4)

Safety Data

• Hazardous Substances Data: 35898-29-4(Hazardous Substances Data)

Upstream product

• 769-78-8 vinyl benzoate 
• 50-89-5 thymidine 
• 1374759-46-2 5,6-bis-TBDMS-5,6-dihydro-5-hydroxy-6-(2,5-dimethoxythiophenyl)thymidine 
• 373391-49-2 Benzoic acid (2R,3S,5R)-3-hydroxy-5-((5R,6S)-6-hydroxy-5-methyl-2,4-dioxo-tetrahydro-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 942-89-2 Acetone O-benzoyloxime 
• 50-89-5 (+/-)-thymidine 
• 65-85-0 benzoic acid 

Downstream Products

• 139432-97-6 5'-O-benzoyl-3'-O-(methylthiomethyl)thymidine 
• 104768-97-0 5'-O-benzoyl-3'-O-methoxymethylthymidine 
• 115244-25-2 C₄₁H₃₉N₄O₁₃PS₂ 
• 142068-19-7 Benzoic acid (2R,3S,5R)-3-(diisopropylamino-methoxy-phosphanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 165047-02-9 ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl benzoate 
• 1225463-25-1 5'-O-benzoyl-3'-O-(tetrahydrofuranyl)thymidine 
• 1225463-21-7 5'-O-benzoyl-3'-O-(tetrahydropyranyl)thymidine 
• 1225463-23-9 5'-O-benzoyl-3'-O-(4-methoxytetrahydropyranyl)thymidine 
• 73189-04-5 3'-O-triphenylmethylthymidine 
• 1465077-11-5 C₃₆H₃₂N₂O₆ 
• 76054-81-4 3'-O-(4,4'-dimethoxytrityl)thymidine 
• 50-89-5 thymidine 
• 17331-53-2 3'-O-benzoylthymidine 

Relevant articles and documents

A useful and versatile procedure for the acylation of nucleosides through an enzymatic reaction

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Independent Generation and Reactivity of Thymidine Radical Cations

Thymidine radical cation (1) is produced by ionizing radiation and has been invoked as an intermediate in electron transfer in DNA. Previous studies on its structure and reactivity have utilized thymidine as a precursor, which limits quantitative product analysis because thymidine is readily reformed from 1. In this investigation, radical cation 1 is independently generated via β-heterolysis of a pyrimidine radical generated photochemically from an aryl sulfide. Thymidine is the major product (33%) from 1 at pH 7.2. Diastereomeric mixtures of thymidine glycol and the corresponding 5-hydroxperoxides resulting from water trapping of 1 are formed. Significantly lower yields of products such as 5-formyl-2′-deoxyuridine that are ascribable to deprotonation from the C5-methyl group of 1 are observed. Independent generation of the N3-methyl analogue of 1 (NMe-1) produces considerably higher yields of products derived from water trapping, and these products are formed in much higher yields than those attributable to the C5-methyl group deprotonation in NMe-1. N3-Methyl-thymidine is, however, the major product and is produced in as high as 70% yield when the radical cation is produced in the presence of excess thiol. The effects of exogenous reagents on product distributions are consistent with the formation of diffusively free radical cations (1, NMe-1). This method should be compatible with producing radical cations at defined positions within DNA.

A mild, efficient and regioselective enzymatic procedure for 5′-O-benzoylation of 2′-deoxynucleosides

Lipase from Candida antarctica B catalyzes the selective monobenzoylation at the 5′-hydroxyl group of 2′-deoxynucleosides using vinyl benzoate as acyl transfer reagent in quantitative yields. The industrial suitability of this process via the reclaim and reuse of enzyme and vinyl benzoate has been demonstrated.