139649-31-3

Upstream product

• 55018-60-5 3',5'-O-(triphenylphosphoranediyl)adenosine 
• 65-85-0 benzoic acid 
• 51549-15-6 2',3',5'-tri-O-benzoyladenosine 
• 93135-70-7 2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate 
• 58-61-7 adenosine 
• 109153-46-0 N₆-isobutyryladenine 
• 98-88-4 benzoyl chloride 
• 362-75-4 2',3'-isopropylidene adenosine 
• 6984-53-8 N⁶,2',3',5'-tetra-O-benzoyladenosine 
• 4005-49-6 N-benzoyladenine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 40601-48-7 5'-O-benzoylinosine 
• 137103-02-7 5'-O-benzoyl-2',3'-O-sulfinyladenosine 
• 67523-54-0 O^5'-benzoyl-O^2',O^3'-(triphenyl-λ⁵-phosphanediyl)-adenosine 

Relevant academic research and scientific papers

Adenosine analogs as inhibitors of tyrosyl-tRNA synthetase: Design, synthesis and antibacterial evaluation

Herein we describe the synthesis and evaluation of a series of adenosine analogs for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Out of these compounds, compound c6 has much stronger antibact

One-flow, multistep synthesis of nucleosides by Bronsted acid-catalyzed glycosylation

Nucleosides in flow: A general, scalable method of Bronsted acid-catalyzed nucleoside formation is described. Because of the high reaction temperatures readily available to the flow reaction format, mild Bronsted acids, particularly pyridinium triflates, can be used. A one-flow multistep synthesis of unprotected nucleosides is also reported (see scheme).

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5' and 8

A number of 5', N6- and C8, N6-disubstituted adenosine analogs was synthesized and tested for inhibition of trypanosomal glyceraldehyde 3- phosphate dehydrogenase. The most active compound, N6-(3-methyl-2-buteny

Partial Protection of Carbohydrate Derivatives. Part 4. Regioselective 2'-O-Deacylation of Fully Acylated Purine and Pyrimidine Ribonucleosides with Hydroxylaminium Acetate

Like hydrazine hydrate, hydroxylamine was found to be useful for the regioselective 2'-O-deacylation of fully acylated purine and pyrimidine ribonucleosides as its salt with acetic acid; the partial O-deacylation reactions (which were not accompanied by undesirable discolouration as happens with hydrazine hydrate) gave the corresponding di-O-acylribonucleosides in superior yields; e.g. 2',3'-di-O-benzoyladenosine (74percent yield), 3',5'- (64percent yield) and 2',5'-di-O-benzoyl-N6-benzyladenosine (63percent yield on performing the reaction in ethanol), N2,3',5'-tri-O-benzoylguanosine (66percent yield), N2,2',5'-tri-isobutyrylguanosine (48percent yield), and 3',5'-di-O-benzoyluridine (61percent yield) were obtained using hydroxylaminium acetate in pyridine.Treatment of fully acetylated ribonucleosides with an excess of hydroxylaminium acetate gave the corresponding 5'-O-acetylribonucleosides in quantitative yields.The excellent regioselectivity observed in the present partial O-decyclation was confirmed on the basis of chromatographic separation; the mixtures of di-O-acylribonucleosides, which had already been equilibrated in pyridine, were re-equilibrated on the silica gel during separation, e.g. a 70 : 30 mixture of 3',5'- and 2',5'-di-O-benzoyladenosine was completely converted into the former based on 1H n.m.r spectroscopy.The acetates of 9-β-D-xylo- and -arabino-furanosyladenine were also found to give predominantly the corresponding 3',5'-diacetates on hydroxylaminolysis.

Studies on Nucleosides and Nucleotides. VIII. Preparation and Reactions of Triphenylphosphoranediylnucleosides

The reaction of uridine, N4-benzoylcitidine, guanosine, and N6-p-toluoyladenosine with diethyl azodicarboxylate and triphenylphosphine resulted in the formation of the corresponding 2',3'-O-(triphenylphosphoranediyl)cyclonucleosides.On the other hand, adenosine afforded, under similar conditions, 3',5'-O-(triphenylphosphoranediyl)adenosine (19).The difference can be explained in terms of the acidity of base moieties of the nucleosides.The reaction of 2',3'-O-(triphenylphosphoranediyl)-O2,5'-cyclouridine, N4-benzoyl-2',3'-O-(triphenylphosphoranediyl)-O2,5'-cyclocytidine, 2',3'-O-(triphenylphosphoranediyl)-N3,5'-cycloguanosine, or N6-p-toluoyl-2',3'-O-(triphenylphosphoranediyl)-N3,5'-cycloadenosine with nucleophiles and with electrophiles addorded the corresponding nucleoside derivatives with free 2'- and 3'-hydroxyl groups.Thus the 2',3'-O-triphenylphosphoranediyl group serves as a protecting group which is readily removed during work-up of the reaction products. 19 reacted with phenyl isocyanate to give 5'-O-phenylcarbamoyladenosine and N6,5'-O-bis(phenylcarbamoyl)adenosine.The reaction of 19 with diphenylketene also afforded acyladenosines with free 2'- and 3'-hydroxyl groups.These results suggested that 3',5'-O-triphenylphosphoranediyl group activates the 5'-carbon atom of adenosine.