3676-72-0

Basic information

• Product Name: N2-Benzoyl-D-guanosine
• Synonyms: N2-BENZOYLGUANOSINE;N2-Benzoyl-D-guanosine;N(sup 2)benzoylguanosine;N-(1,6-Dihydro-6-oxo-9-β-D-ribofuranosyl-9H-purin-9-yl)benzaMide;2N-Benzoyl Guanosine;N2-Benzoylguanosine;N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide
• CAS NO: 3676-72-0
• Molecular Formula: C₁₇H₁₇N₅O₆
• Molecular Weight: 387.35
• Product Categories: Bases & Related Reagents;Nucleotides;Aromatics;Heterocycles
• Mol File: 3676-72-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 255-256
• Appearance: Off-white solid
• Density: 1.8 g/cm³
• Refractive Index: 1.809
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: N2-Benzoyl-D-guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: N2-Benzoyl-D-guanosine(3676-72-0)
• EPA Substance Registry System: N2-Benzoyl-D-guanosine(3676-72-0)

Safety Data

• Hazardous Substances Data: 3676-72-0(Hazardous Substances Data)

Usage

Description

N2-Benzoyl-D-guanosine is a chemical compound derived from the nucleoside guanosine, with a benzoyl group attached to the nitrogen at the second position. It is an off-white solid and serves as a crucial building block in the synthesis of oligoribonucleotides.

Uses

Used in Pharmaceutical Industry:
N2-Benzoyl-D-guanosine is used as a building block for the synthesis of oligoribonucleotides, which are short sequences of ribonucleic acids (RNA). These oligoribonucleotides have various applications in the pharmaceutical industry, including the development of antisense drugs, RNA interference (RNAi) therapies, and the creation of artificial ribonucleic acid molecules for research purposes.
Used in Research and Development:
In the field of research and development, N2-Benzoyl-D-guanosine is utilized for the synthesis of modified RNA molecules with specific properties. These modified RNA molecules can be used to study the structure, function, and interactions of RNA in biological systems, contributing to a better understanding of RNA biology and its role in various diseases.
Used in Diagnostics:
N2-Benzoyl-D-guanosine can also be employed in the development of diagnostic tools and assays that rely on the detection or manipulation of RNA molecules. These diagnostic applications can help in the early detection of diseases, monitoring of treatment responses, and the study of disease progression.
Overall, N2-Benzoyl-D-guanosine plays a significant role in various applications across the pharmaceutical, research, and diagnostic industries due to its importance in the synthesis of oligoribonucleotides and modified RNA molecules.

InChI:InChI=1/C17H17N5O6/c23-6-9-11(24)12(25)16(28-9)22-7-18-10-13(22)19-17(21-15(10)27)20-14(26)8-4-2-1-3-5-8/h1-5,7,9,11-12,16,23-25H,6H2,(H2,19,20,21,26,27)/t9-,11-,12-,16-/m1/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 532-55-8 Benzoyl isothiocyanate 
• 2627-69-2 AICA riboside 
• 118-00-3 G 
• 53274-35-4 2',3',5'-O-Trisguanosine 
• 112156-61-3 5-(3-Benzoyl-thioureido)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-imidazole-4-carboxylic acid amide 
• 80015-56-1 2'-O-(4-methoxybenzyl)-N²-benzoylguanosine 
• 28288-50-8 N²,O^2',O^3',O^5'-tetrabenzoylguanosine 

Downstream Products

• 87985-94-2 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-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester 
• 88015-19-4 Phosphoric acid (2R,3R,4R,5R)-5-(2-benzoylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester 
• 87985-93-1 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 87985-92-0 2'-O-(4-methoxybenzyl)-3',5'-di-O-acetyl-N²-benzoylguanosine 
• 81794-14-1 N-{9-[(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 81794-15-2 N-{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-benzamide 
• 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 
• 72409-45-1 N²-Benzoyl-2',3'-bis-O-(tert-butyldimethylsilyl)guanosin 
• 72409-43-9 N²-Benzoyl-2'-O-(tert-butyldimethylsilyl)guanosin 
• 72409-44-0 N²-Benzoyl-3'-O-(tert-butyldimethylsilyl)guanosin 
• 87125-05-1 2-N-benzoyl-2'-O-tetrahydropyranyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine 

Relevant articles and documents

New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors

Design and development of nucleoside analogs is an established strategy in the antiviral drug discovery field. Nevertheless, for many viruses the coverage of structure-activity relationships (SAR) in the nucleoside chemical space is not sufficient. Here we present the nucleoside SAR exploration for tick-borne encephalitis virus (TBEV), a member of Flavivirus genus. Promising antiviral activity may be achieved by introduction of large hydrophobic substituents in the position 6 of adenosine or bulky silyl groups to the position 5′. Introduction of methyls to the ribose moiety does not lead to inhibition of TBEV reproduction. Possible mechanisms of action of these nucleosides include the inhibition of viral entry or interaction with TBEV non-structural protein 5 methyltransferase or RNA-dependent RNA polymerase domains.

Synthesis of Guanosines and Deoxyguanosines from 5-amino-1-(β-D-ribofuranosyl)imidazole-4-carboxamide ('AICA-riboside')

Methods are described for the synthesis of 15N-labelled guanosines and deoxyguanosines, suitable for incorporation into oligonucleotides.The 15N is located at N-1 (e.g. guanosine 1a and deoxyguanosine 1b> or at the NH2 (e.g. guanosine 1

An Improved Method for the Application of the 4-Methoxybenzyl Group to Protect the 2'-Hydroxyl Group in the Ribonucleotide Synthesis by TFA-acidolysis

The cleavage of the 4-methoxybenzyl group from the 2'-OH-position of ribonucleosides by the hydrogenation with different Pd-catalysts as well as trifluoroacetic acid has been studied in detail.During hydrogenation, side reactions at the base residue of cytidine occurred which, however, could be extensively suppressed by PdCl2 catalysis.More practicable results were obtained with trifluoroacetic acid in the presence of cation scavengers, allowing smoothly to convert a series of 2'-methoxybenzyl ribonucleotides to the homogeneous deprotection products.