94189-75-0

Basic information

• Product Name: N³-benzoyl thymidine
• Synonyms: N³-benzoyl thymidine
• CAS NO: 94189-75-0
• Molecular Weight: 346.34
• Mol File: 94189-75-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: N³-benzoyl thymidine(CAS DataBase Reference)
• NIST Chemistry Reference: N³-benzoyl thymidine(94189-75-0)
• EPA Substance Registry System: N³-benzoyl thymidine(94189-75-0)

Safety Data

• Hazardous Substances Data: 94189-75-0(Hazardous Substances Data)

Upstream product

• 50-89-5 thymidine 
• 146952-74-1 5'-O-triethylsilylthymidine 
• 98-88-4 benzoyl chloride 
• 10457-18-8 3',5'-bis-O-(trimethylsilyl)-thymidine 
• 124130-15-0 N³,3',5'-O-tribenzoyl thymidine 
• 115351-22-9 3',5'-bis-O-(trimethylsilyl)-N³-benzoylthymidine 

Downstream Products

• 106502-50-5 3-Benzoyl-1-{(2R,4S,5R)-4-hydroxy-5-[(3-imidazol-1-ylmethyl-phenyl)-bis-(4-methoxy-phenyl)-methoxymethyl]-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 50-89-5 thymidine 
• 1360057-57-3 5'-O-dimethoxytrityl-3'-(propyn-3-yl) N₃-benzoylthymidine 
• 102573-69-3 5'-O-(4-4'-dimethoxytrityl)-N³-benzoyl thymidine 
• 913697-72-0 5'-O-dimethoxytrityl-N³-benzoylthymidine-3'-O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite 
• 123884-04-8 3-Benzoyl-1-((2R,4S,5R)-4-methoxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 123884-05-9 3'-O-methyl-5'-O-tritylthymidine 
• 108895-42-7 3'-O-methylthymidine 
• 94189-82-9 C₆₈H₆₁N₄O₁₆PS 
• 94189-77-2 triethylammonium S-phenyl 5'-O-(4,4'-dimethoxytrityl)-3-N-benzoylthymidine 3'-phosphorothioate 
• 94219-35-9 C₇₃H₆₇N₅O₁₆P₂S₃ 
• 94189-83-0 C₇₃H₆₆N₄O₁₆P₂S₃ 
• 106502-55-0 Thiophosphoric acid O-{(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(3-imidazol-1-ylmethyl-phenyl)-bis-(4-methoxy-phenyl)-methoxymethyl]-tetrahydro-furan-3-yl} ester S-phenyl ester; compound with triethyl-amine 
• 106469-72-1 Dithiophosphoric acid O-{(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(3-imidazol-1-ylmethyl-phenyl)-bis-(4-methoxy-phenyl)-methoxymethyl]-tetrahydro-furan-3-yl} ester S,S'-diphenyl ester 

Relevant articles and documents

Design and synthesis of dephosphono dna analogues containing 1,2,3-triazole linker and their uv-melting studies with DNA/RNA

This article describes the synthesis of 3/5 linked 1,2,3-triazolyl dithymidine derivatives, their incorporation into oligonucleotides, and evaluation of their thermal stabilities toward complementary DNA/RNA. Copyright Taylor and Francis Group, LLC.

Synthesis of 3'O-(2-cyanoethyl)-2'-deoxythymidine-5'-phosphate as a model compound for evaluation of Cyanoethyl Cleavage

An essential and challenging task during the development of our sequencing-by-synthesis (SBS) technique is the evaluation of efficient cyanoethyl (CE) cleavage conditions. For this purpose 3'-O-(2-cyanoethyl)-2'- deoxythymidine-5'-phosphate as a model compound as well as a short DNA oligomer bearing the CE function as terminal group were synthesized and used for various deprotection experiments. As it is already known for 2'-O-CE-protected RNA oligonucleotides, the CE function can be cleaved with tetrabutylammonium fluoride (TBAF) in THF. Indeed, by using 3'-O-(2-cyanoethyl)-2'-deoxythymidine- 5'-phosphate as a simple model compound for cleavage tests, we found out that the 3'-O-CE function is quantitatively cleaved with 1 m TBAF in THF. However, the CE group is also cleaved by other small bases like hydroxy groups under alkaline conditions. The CE cleavage with TBAF in THF gives the fastest and quantitative removal of the CE group under mild conditions for our sequencing-by-synthesis (SBS) application. The efficient removal of the 3'-CE group is crucial for the proof-of-principle of our SBS approach using dye-labeled 3'-CE-blocked dNTPs, which is currently under investigation. Herein we describe the application of 3'-O-(2-cyanoethyl)-2'-deoxythymidine-5'- phosphate as model compound for the development of reversible terminators for the SBS technique. Furthermore we suggest that nucleoside phosphates bearing any removable 3'-modification might be suitable model compounds for cleavage studies in a heterogeneous environment comparable to an oligonucleotide/aprotic solvent system.

New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation

An improved procedure for the synthesis of N-benzoyl-2′,3′-O-isopropylidene uridine via one-step selective N-benzoylation of 2′,3′-O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described. De-N-benzoylation of N-benzoylated thymidine and uridine derivatives can be conveniently effected under neutral conditions, by heating with benzyl alcohol.