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
• Article Data: 6

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

N,N,2'',3''-Tetrabenzoyladenosine, is a Multibenzoylated nucleoside, serving as the key starting materials in the synthesis of small oligonucleotides such as dinucleotides and trinucleotides. It can be used for the preparation of trinucleotides 2-5 A, 2-5 core, and their analogs, which are known for their antiviral and antitumor activity.

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.

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

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