31501-22-1

Upstream product

• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 98-88-4 benzoyl chloride 
• 951-77-9 2'-Deoxycytidine 
• 93-97-0 benzoic acid anhydride 
• 613-90-1 benzoyl cyanide 
• 64339-87-3 N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine 
• 26661-13-2 4-N-benzoylcytosine 

Downstream Products

• 20963-97-7 3',5'-di-O-benzoyl-2'-deoxycytidine 
• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 31615-99-3 3',5'-Di-O-benzoyl-2'-deoxyuridine 
• 951-77-9 2'-Deoxycytidine 
• 67219-55-0 4-N-Benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)cytidine 
• 78111-51-0 C₆₆H₆₃Cl₂N₉O₁₇P₂ 
• 78098-93-8 C₆₆H₆₃Cl₂N₉O₁₇P₂ 
• 85240-12-6 C₆₃H₆₀Cl₂N₈O₁₇P₂ 
• 85240-13-7 C₆₃H₆₀Cl₂N₈O₁₇P₂ 
• 76964-04-0 [1,2,4]Triazol-1-yl-phosphonic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 
• 80817-38-5 N⁴-benzoyl-2'-deoxycytidine-3'-O-(2-chlorophenyl-2-cyanoethyl)phosphate 
• 80817-35-2 N-4-benzoyl-5'-O-(dimethoxytrityl)-2'-deoxycitidine 3'-(o-chlorophenyl β-cyanoethyl phosphate) 
• 81187-02-2 4,4'-dimethoxytrityl-4-N-benzoyl-2'-deoxycytidine-3'-O-(2-chlorophenyl)phosphate 

Relevant academic research and scientific papers

Microwave assisted high yielding preparation of N-protected 2′-deoxyribonucleosides useful for oligonucleotide synthesis

A rapid and high yielding method for the synthesis of precursors of synthons for DNA synthesis, N-protected 2′-deoxyribonucleosides is described, which occur under mild conditions using microwave irradiation. The desired material, N-protected nucleosides, was obtained in 93-96% yield in few minutes. The final products were then characterized by H-NMR and MALDI-TOF and compared with the standard samples. The method is amenable to small to moderate scale of synthesis.

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.

'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.

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.

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.

Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters

(Chemical Equation Presented) N,O-Peracylated cytidine and 2′-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125°C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

Simplified Liquid-Phase Preparation of Four Decadeoxyribonucleotides and their Preliminary Spectroscopic Characterization

Four self-complementary decadeoxyribonucleotides, dApTpApTpApTpApTpApT,dApTpApTpCpGpApTpApT, dApTpApTpGpCpApTpApT and dApApApApApTpTpTpTpT, were chemically synthesized by the phosphotriester procedure.Efforts were concentrated on keeping the procedure as simple as possible, concomitant with obtaining high-purity products at each step of the process.The decamers were elaborated from the 3'-end, starting with a 3'-O-benzoylated monomer according to the scheme: monomer + monomer -> dimer + dimer -> tetramer + dimer -> hexamer + tetramer -> decamer.Putity of intermediates and of the fully blocked decamers were monitored by chromatography and by 300-MHz 1H-NMR. spectroscopy.The deblocked decadeoxyribonucleotides were characterized by their UV., CD., and 1H-NMR. spectra.

N-ACYL PROTECTING GROUPS FOR DEOXYNUCLEOTSIDES A QUANTITATIVE AND COMPARATIVE STUDY

A detailed study in search for suitable N-acyldeoxy-nucleosides which could serve as building blocks for the stepwise synthesis of deoxyoligonucleotides was undertaken.Several acyl groups namely 4-t-butylphenylacetyl, 4-t-butylphenoxyacetyl, 4-chlorobenzoyl, 3,4-dichlorobenzoyl, 2-methyl-benzoyl, 2,4-dimethylbenzoyl, nicotinoyl, 4-t-butylbenzoyl and 4-phenylazobenzoyl have been used for the protection of the exocyclic amino groups of deoxynucleosides.Interesting data concerning the stability of N-acyl groups towards a potent deacylating system (0.2N NaOH/MeOH) are presented.