N6-Dibenzoyladenosine 2',3'-Dibenzoate

Base Information

• Chemical Name: N6-Dibenzoyladenosine 2',3'-Dibenzoate
• CAS No.: 58463-04-0
• Molecular Formula: C38H29N5O8
• Molecular Weight: 683.677
• Mol file: 58463-04-0.mol

Synonyms:[(2R,3R,5R)-4-benzoyloxy-5-[6-(dibenzoylamino)purin-9-yl]-2-(hydroxymethyl)oxolan-3-yl] benzoate;

Chemical Property of N6-Dibenzoyladenosine 2',3'-Dibenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 183 °C
• Boiling Point: 878.975oC at 760 mmHg
• Flash Point: 485.387oC
• PSA: 163.04000
• Density: 1.411g/cm3
• LogP: 4.65440

Purity/Quality:

97% ^*data from raw suppliers

N6-Dibenzoyladenosine 2',3'-Dibenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of N6-Dibenzoyladenosine 2',3'-Dibenzoate

There total 6 articles about N6-Dibenzoyladenosine 2',3'-Dibenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

O5'-tert-butyldimethylsilyl-N6,N6,O2',O3'-tetrabenzoyladenosine (1031809-76-3) → N6,N6,2'-O,3'-O-tetrabenzoyladenosine (58463-04-0)

Guidance literature:

With SO₃H silica gel; In chloroform; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2017.07.047

Reference yield: 99.0%

benzoyl chloride (98-88-4) + adenosine (58-61-7) → N6,N6,2'-O,3'-O-tetrabenzoyladenosine (58463-04-0)

Guidance literature:

adenosine; With pyridine; tert-butyldimethylsilyl chloride; at 0 - 20 ℃; for 9h;

benzoyl chloride; at 0 - 20 ℃;

With trifluoroacetic acid; In tetrahydrofuran; water; at 20 ℃; for 3h; Time;

Reference yield: 80.0%

C59H47N5O10 (1031809-74-1) → N6,N6,2'-O,3'-O-tetrabenzoyladenosine (58463-04-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol802815g

upstream raw materials:

O^5'-tert-butyldimethylsilyl-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine

C₅₉H₄₇N₅O₁₀

5'-(O-tert-butyldimethylsilyl)adenosine

adenosine

Downstream raw materials:

N⁶-Benzoyl-3',5'-O-TIPDSi-P-methyl-P-thioadenylyl-(2'-5')-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosine

N⁶-Benzoyl-3',5'-O-TIPDSi-P-methyl-P-thioadenylyl-(2'-5')-N⁶,N⁶,O^2',O^3'-tetrabenzoyladenosin

C₈₁H₆₀Br₂ClN₁₀O₁₆P

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