35898-30-7

Basic information

• Product Name: 3',5'-DI-O-BENZOYLTHYMIDINE
• Synonyms: 3',5'-DI-O-BENZOYLTHYMIDINE;thymidine 3',5'-dibenzoate;3'-O,5'-O-Dibenzoylthymidine
• CAS NO: 35898-30-7
• Molecular Formula: C₂₄H₂₂N₂O₇
• Molecular Weight: 450.44
• EINECS: 252-786-1
• Mol File: 35898-30-7.mol

Chemical Properties

• Appearance: /
• Density: 1.39 g/cm³
• CAS DataBase Reference: 3',5'-DI-O-BENZOYLTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-DI-O-BENZOYLTHYMIDINE(35898-30-7)
• EPA Substance Registry System: 3',5'-DI-O-BENZOYLTHYMIDINE(35898-30-7)

Safety Data

• Hazardous Substances Data: 35898-30-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3',5'-DI-O-BENZOYLTHYMIDINE is used as a reagent in organic synthesis for the preparation of complex organic molecules, leveraging its unique structural features to facilitate specific chemical reactions.
Used in Biochemistry Research:
In biochemistry, 3',5'-DI-O-BENZOYLTHYMIDINE is utilized as a building block for the synthesis of nucleoside analogues, which are essential for studying the structure and function of nucleic acids and their components.
Used in Antiviral and Antitumor Drug Development:
3',5'-DI-O-BENZOYLTHYMIDINE is used as a potential therapeutic agent for its antiviral and antitumor properties, being investigated for its ability to inhibit the growth of certain cancer cells and its potential application in treating viral infections.
Used in Enzyme Substrate Research:
3',5'-DI-O-BENZOYLTHYMIDINE serves as a substrate for enzymes involved in nucleoside metabolism, making it a valuable tool for studying the biochemical pathways and mechanisms of nucleoside processing in cells, which is crucial for understanding cellular functions and developing targeted therapies.
Overall, 3',5'-DI-O-BENZOYLTHYMIDINE's applications span across various scientific disciplines, highlighting its importance in research and development within the pharmaceutical industry.

Upstream product

• 98-88-4 benzoyl chloride 
• 50-89-5 thymidine 
• 175024-33-6 C₂₃H₂₉N₂O₇P 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 182004-59-7 3',5'-di-O-benzoyl-2'-O-[3-(trifluoromethyl)benzoyl]-5-methyluridine 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 613-90-1 benzoyl cyanide 
• 93-97-0 benzoic acid anhydride 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 50503-53-2 5-methyl-2,4-bis-trimethylsilanyloxy-pyridine 
• 65-71-4 thymin 
• 51255-12-0 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-D-erythro-pentafuranose 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 
• 108647-88-7 ((2R,3S)-3-(benzoyloxy)-5-methoxytetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 93841-35-1 O^3'_,O5'-dibenzoyl-4-thio-thymidine 
• 137121-87-0 α/β-D-thymidine 
• 99692-47-4 1-[1-((2R,4S,5R)-4-Benzoyloxy-5-benzoyloxymethyl-tetrahydro-furan-2-yl)-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl]-3-methyl-3H-imidazol-1-ium; chloride 
• 7236-57-9 4-thiothymidine 
• 31615-99-3 3',5'-Di-O-benzoyl-2'-deoxyuridine 
• 99680-04-3 C₃₀H₂₅ClN₂O₆S 
• 122567-95-7 1-(5-O-trityl-2-deoxy-β-D-threo-pentofuranosyl)-4-thiothymine 
• 122567-96-8 Methanesulfonic acid (2R,3R,5R)-5-(5-methyl-2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl ester 
• 838-07-3 5-methyldeoxycytidine 
• 25406-44-4 N,5-dimethyl-2’-deoxycytidine 
• 123103-76-4 O^3'_,O5'-dibenzoyl-N⁴-hydroxy-5-methyl-2'-deoxy-cytidine 
• 50-89-5 thymidine 
• 59090-48-1 5-(azidomethyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Photocycloaddition of benzoylated 2'-deoxyribonucleoside to 2,3-dimethyl-2-butene

The photochemical reactions of 3',5'-dibenzoyl-2'-deoxyuridine and -thymidine with 2,3-dimethyl-2-butene by upon ultraviolet (UV) irradiation in acetone have been investigated. Each reactant gave a pair of diastereomers in good yield. After recrystallization, mixed crystals of diastereomers could be isolated and purified. An X-ray analysis of a mixed crystal of the thymidine derivative (3b) showed a pair of diastereomers (A and B) composing a unit cell.

Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing

We report a series of 2′-deoxyribonucleoside triphosphates bearing dicarba-nido-undecaborate ([C2B9H11]1-), [3,3′-iron-bis(1,2-dicarbollide)]- (FESAN, [Fe(C2B9H11)2]2-) or [3,3′-cobalt-bis(1,2-dicarbollide)]- (COSAN, [Co(C2B9H11)2]2-) groups prepared either through the Sonogashira cross-coupling or the CuAAC click reaction. The modified dNXTPs were substrates for KOD XL DNA polymerase in enzymatic synthesis of modified DNA through primer extension (PEX). The nido-carborane- and FESAN-modified nucleotides gave analytically useful oxidation signals in square-wave voltammetry and were used for redox labeling of DNA. The redox-modified DNA probes were prepared by PEX using tailed primers and were hybridized to electrode (gold or glassy carbon) containing capture oligonucleotides. The combination of nido-carborane- and FESAN-linked nucleotides with 7-ferrocenylethynyl-7-deaza-dATP and 7-deaza-dGTP allowed polymerase synthesis of DNA fully modified at all four nucleobases, and each of the redox labels gave four differentiable and ratiometric signals in voltammetry. Thus, the combination of these four redox labels constitutes the first fully orthogonal redox coding of all four canonical nucleobases, which can be used for determination of nucleobase composition of short DNA stretches in one simple PEX experiment with electrochemical readout.

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.

Continuous flow photochemistry for the rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A new photochemical flow reactor has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly improved both the efficiency and selectivity of the reaction, with the streamlined multi-step sequence directly furnishing the highly desired unprotected deoxynucleosides.

Continuous flow photocatalysis enhanced using an aluminum mirror: Rapid and selective synthesis of 2′-deoxy and 2′,3′-dideoxynucleosides

A unique photochemical flow reactor featuring quartz tubing, an aluminum mirror and temperature control has been developed for the photo-induced electron-transfer deoxygenation reaction to produce 2′-deoxy and 2′,3′-dideoxynucleosides. The continuous flow format significantly increased the efficiency and selectivity of the reaction.

Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid

Solubility and benzoylation study of both ribo- and deoxyribonucleosides is reported in a new ionic liquid MoeMIM·TFA; high selectivity for O-benzoylation is achieved.

Benzoyl cyanide: A mild and efficient reagent for benzoylation of nucleosides

Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.

'Green' methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid

Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully extended for highly efficient benzoylation of phenols, aromatic amines, benzyl alcohol, aliphatic diols, 3-aminophenol and 2-aminobenzylalcohol, which indicates the versatility of this benzoylating system.

Mild, efficient, selective and "green" benzoylation of nucleosides using benzoyl cyanide in ionic liquid

Use of benzoyl cyanide (BzCN) for benzoylation of nucleosides has been studied, both in pyridine and in ionic liquid. BzCN in 1-methoxyethyl-3- methylimidazolium methanesulfonate as ionic liquid has been found to be a "green" alternative compared to the pyridine-BzCN system. An efficient and selective benzoylation of nucleosides of both, the 2′-deoxy- and the ribo-series at ambient temperature was accomplished. Copyright Taylor & Francis, Inc.

Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides

The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.