28288-50-8

Basic information

• Product Name: Guanosine, N-benzoyl-, 2',3',5'-tribenzoate
• Synonyms: 2',3',5',N2-tetrabenzoylguanosine;2-N-benzoyl-2',3',5'-tri-O-benzoylguanosine;N2-benzoyl-2',3',5'-tri-O-benzoylguanosine;N2,2'-O,3'-O,5'-O-tetrabenzoylguanosine;N2,2',3',5'-tetrabenzoylguanosine;N2,2',3',5'-tetra-O-benzoylguanosine
• CAS NO: 28288-50-8
• Molecular Formula: C38H29N5O9
• Molecular Weight: 699.676
• Mol File: 28288-50-8.mol

Chemical Properties

• Melting Point: 130-135 °C
• Density: 1.44±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Guanosine, N-benzoyl-, 2',3',5'-tribenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, N-benzoyl-, 2',3',5'-tribenzoate(28288-50-8)
• EPA Substance Registry System: Guanosine, N-benzoyl-, 2',3',5'-tribenzoate(28288-50-8)

Safety Data

• Hazardous Substances Data: 28288-50-8(Hazardous Substances Data)

Upstream product

• 613-90-1 benzoyl cyanide 
• 118-00-3 G 
• 93-97-0 benzoic acid anhydride 
• 86137-69-1 N²,2',3',5'-tetrabenzoyl-O⁶-nitrophenylethylguanosine 

Downstream Products

• 261518-13-2 N²,2'-O,3'-O,5'-O-tetrabenzoyl-6-thioguanosine 
• 62374-25-8 N²,3',5'-tribenzoylguanosine 
• 66781-54-2 2',3',5'-tri-O-acetyl-N²-benzoylguanosine 
• 115264-93-2 C₆₃H₅₃N₈O₁₈P 
• 19325-98-5 2',5'-O,N²-tribenzoylguanosine 
• 86137-71-5 N²-benzoyl-O⁶-p-nitrophenylethylguanosine 
• 87125-07-3 2-N-benzoyl-2'-O-tetrahydropyranyl-5'-O-dimethoxytritylguanosine-3'-(p-chlorophenyl-2-cyanoethyl)phosphate 
• 87125-14-2 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 
• 97626-10-3 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 2-cyano-ethyl ester 
• 87125-05-1 2-N-benzoyl-2'-O-tetrahydropyranyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine 
• 71933-62-5 5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-N²-benzoylguanosine 
• 78842-00-9 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N²-benzoylguanosine 
• 60324-96-1 2'-O-(tetrahydropyranyl)-N²-benzoylguanosine 
• 170935-34-9 N²-benzoyl-6-thioguanosine 

Relevant articles and documents

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.

Incorporation Of 6-Thioguanosine Into Oligoribonucleotides

The preparation of N2-benzoyl-S6-cyanoethyl-6-thioguanosine and its incorporation into oligoribonucleotides, using standard phosphoramidite methods, is described. 6-Thioguanosine has been incorporated into the three guanosine sites of the central core of the hammerhead ribozyme resulting in 2- to 9-fold reductions in catalytic activity.

THE p-NITROPHENYLETHYL (NPE) GROUP. A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES

The syntheses of new monomeric building blocks for oligonucleotide synthesis via the phosphotriester approach containing the p-nitrophenylethyl group for phosphate and aglycone protection are described.Blocking of the amide function in guanosines at O6 can be achieved by the Mitsunobu reaction forming the corresponding O6-p-nitrophenylethyl derivatives (4,5,10).Sugar-protected thymidine (16) and uridine (17) have been alkylated at O4 in an SN1-type reaction by p-nitrophenylethyl iodide-silver carbonate in benzene to form the O4-p-nitrophenylethyl derivatives (18,19).Protection of the amino group in 2'-deoxycytidine (25) and cytidine (26) can be performed directly by 1-(p-nitrophenylethoxycarbonyl)-benzotriazole in DMF to obtain the corresponding carbamates (27,28) as a new type of N4-acylated cytidine derivative. p-Nitrophenylethoxycarbonylation of the amino group in 2'-deoxyadenosine (33) and adenosine (34) requires previous sugar protection by acyl or silyl groups and can then be achieved by p-nitrophenylethyl chloroformate or better by 1-methyl-3-p-nitrophenylethoxycarbonylimidazolium chloride to form N6-p-nitrophenylethoxycarbonyladenosines (38,39,40,42).The various p-nitrophenylethyl blocking groups are stable under mild hydrolytic conditions (e.g. ammonia and triethylamine) but can be cleaved selectively by DBU or DBN in aprotic solvents. 5'-O-Monomethoxytritylation (12,29,43) as well as phosphorylations at the 3'-OH group can be effected to give the corresponding 3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphotriesters (13,22,30,44) also in high yields.Oximate cleavage of the latter compounds to the phosphodiesters (14,24,32,46) and detritylation to the 5'-unblocked phosphotriesters (15,23,31,45) do not affect the aglycone protecting groups, thereby demonstrating their general versatility.The newly synthesized compounds have been characterized on the basis of their elementary analyses (C,N,H), and UV- and 1H-HMR-spectra.

SYNTHESIS OF O6-p-NITROPHENYLETHYL GUANOSINE AND 2'-DEOXYGUANOSINE DERIVATIVES

The p-nitrophenylethyl group is introduced into the O6-position of 2'-deoxyguanosine and guanosine via the Mitsunobu-reaction to yield valuable building blocks for oligonucleotide syntheses.