58463-04-0

Basic information

• Product Name: N6-Dibenzoyladenosine 2',3'-Dibenzoate
• Synonyms: N6-Dibenzoyladenosine 2',3'-Dibenzoate;N6-Dibenzoyladenosine 2',3'-Dibenzoate
• CAS NO: 58463-04-0
• Molecular Formula: C₃₈H₂₉N₅O₈
• Molecular Weight: 683.66556
• Mol File: 58463-04-0.mol

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 878.975°C at 760 mmHg
• Flash Point: 485.387°C
• Appearance: /
• Density: 1.411g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: N6-Dibenzoyladenosine 2',3'-Dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: N6-Dibenzoyladenosine 2',3'-Dibenzoate(58463-04-0)
• EPA Substance Registry System: N6-Dibenzoyladenosine 2',3'-Dibenzoate(58463-04-0)

Safety Data

• Hazardous Substances Data: 58463-04-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N6-Dibenzoyladenosine 2',3'-Dibenzoate is used as a key starting material for the synthesis of small oligonucleotides such as dinucleotides and trinucleotides. These oligonucleotides have potential applications in the development of new drugs and therapies.
Used in Antiviral and Antitumor Applications:
N6-Dibenzoyladenosine 2',3'-Dibenzoate is used for the preparation of trinucleotides 2-5 A, 2-5 core, and their analogs, which are known for their antiviral and antitumor activity. These compounds can be used in the development of treatments for various viral infections and cancer types.

InChI:InChI=1/C38H29N5O8/c44-21-28-30(50-37(47)26-17-9-3-10-18-26)31(51-38(48)27-19-11-4-12-20-27)36(49-28)42-23-41-29-32(42)39-22-40-33(29)43(34(45)24-13-5-1-6-14-24)35(46)25-15-7-2-8-16-25/h1-20,22-23,28,30-31,36,44H,21H2/t28-,30-,31?,36-/m1/s1

Upstream product

• 1031809-76-3 O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine 
• 1031809-74-1 C₅₉H₄₇N₅O₁₀ 
• 69530-93-4 5'-(O-tert-butyldimethylsilyl)adenosine 
• 58-61-7 adenosine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 90191-55-2 N⁶-Benzoyl-3',5'-O-TIPDSi-P-methyl-P-thioadenylyl-(2'-5')-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine 
• 90108-20-6 N⁶-Benzoyl-3',5'-O-TIPDSi-P-methyl-P-thioadenylyl-(2'-5')-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosin 
• 77244-75-8 C₈₁H₆₀Br₂ClN₁₀O₁₆P 
• 75085-70-0 N⁶-Benzoyl-3'-O-tert-butyldimethylsilyl-5'-O-(4-methoxytrityl)adenylyl<2'-P-(2-chlorphenyl)>-5'>-N⁶-benzoyl-3'-O-(tert-butyldimetylsilyl)adenylyl<2'-P-(2-chlorphenyl)>-5'>-N⁶,N⁶,2'-O,3'-O-tetrabenzoyladenosin 
• 75085-71-1 N⁶-Benzoyl-2'-O-tert-butyldimethylsilyl-5'-O-(4-methoxytrityl)adenylyl<3'-P-(2-chlorphenyl)>-5'>-N⁶-benzoyl-3'-O-(tert-butyldimethylsilyl)adenylyl<2'-P-(2-chlorphenyl)>-5'>-N⁶,N⁶,2'-O,3'-O-tetrabenzoyladenosin 
• 75085-69-7 N⁶-Benzoyl-3'-O-tert-butyldimethylsilyl-5'-O-(4-methoxytrityl)adenylyl<2'-P-(2-chlorphenyl)>-5'>-N⁶-benzoyl-2'-O-(tert-butyldimethylsilyl)adenylyl<3'-P-(2-chlorphenyl)>-5'>-N⁶,N⁶,2'-O,3'-O-tetrabenzoyladenosin 
• 95537-78-3 C₈₃H₆₈N₁₁O₁₇P 
• 113297-67-9 N⁶,3'-Dibenzoyl-5'-O-monomethoxytrityladenylyl-(2'->-5')-N⁶,N⁶,2',3'-tetrabenzoyladenosin 
• 81691-48-7 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)adenylyl-(2'->5')-2',3'-di-O-benzoyl-N,N-dibenzoyladenosine P (2-chlorophenyl) ester 
• 113297-65-7 3'-O-Benzoyl-5'-O-trityladenylyl-<2'--5'>-N⁶,N⁶,2',3'-tetrabenzoyladenosine 
• 80727-13-5 N⁶-Benzoyl-3'-O-tert-butyldimethylsilyl-5'-O-(4-methoxytrityl)adenylyl-<2'-P-(2-chlorphenyl)>-5'>-N⁶,N⁶,2'-O,3'-O-tetrabenzoyladenosin 
• 78092-50-9 C₈₉H₇₅ClN₉O₁₉P 
• 100899-71-6 N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine 5'-aldehyde 
• 189145-17-3 C₈₈H₈₀N₁₀O₂₁P₂S 

Relevant articles and documents

Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives

We applied a desilylation procedure using SO3H silica gel, with the surface modified by alkylsulfonic acid groups, to silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a labile glycosyl and C–N bond, respectively, these bonds tolerated the reaction conditions. These outcomes suggested that the desilylation procedure using SO3H silica gel would be applicable to the deprotection of a variety of types of compounds protected by silyl groups. In a gram scale experiment, the desilylation procedure successfully proceeded without the observation of any silyl residue in the crude product.

NUCLEOSIDE ANALOGUES FOR THE TREATMENT OF A VIRAL INFECTION, AND METHOD FOR EVALUATING THE SENSITIVITY TO SAID TREATMENT

The present invention describes the use of nucleoside analogues for the treatment of viral infections, in particular of an HIV infection, and also compositions comprising at least one of these analogues, and a method for evaluating the sensitivity to said treatment.

Preparation of fluorinated RNA nucleotide analogs potentially stable to enzymatic hydrolysis in RNA and DNA polymerase assays Dedicated to Dr. Teruo Umemoto on the occasion of receiving the ACS Award for Creative Work in Fluorine Chemistry.

Analogs of ribonucleotides (RNA) stable to enzymatic hydrolysis were prepared and characterized. Computational investigations revealed that this class of compounds with a modified triphosphate exhibits the correct polarity and minimal steric effects compa

Design and synthesis of α-carboxy phosphononucleosides

Rhodium catalyzed O-H insertion reactions employing α- diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5′-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

Efficient chemical synthesis of AppDNA by adenylation of immobilized DNA-5'-monophosphate

AppDNA is an intermediate in enzyme-catalyzed DNA ligation reactions, and its efficient enzymatic synthesis requires a donor-template duplex of at least 11 base pairs in length. An efficient chemical synthesis of AppDNA with the coupling of an adenosine 5

Novel synthetic approach to multibenzoylated nucleosides

An improved and highly efficient synthetic approach to multibenzoylated nucleosides bearing free 5'-hydroxyl groups is described here. By employing t-butyldimethylsilyl (TBDMS) rather than the more commonly used dimethoxytrityl (DMTr) as a temporary 5'-OH