N-acetyl-9-(2,3,5-tri-O-acetylpentofuranosyl)-9H-purin-6-amine

Base Information

• Chemical Name: N-acetyl-9-(2,3,5-tri-O-acetylpentofuranosyl)-9H-purin-6-amine
• CAS No.: 7387-58-8
• Molecular Formula: C₁₈H₂₁N₅O₈
• Molecular Weight: 435.393
• Mol file: 7387-58-8.mol

Synonyms:

Chemical Property of N-acetyl-9-(2,3,5-tri-O-acetylpentofuranosyl)-9H-purin-6-amine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.56g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-acetyl-9-(2,3,5-tri-O-acetylpentofuranosyl)-9H-purin-6-amine

There total 2 articles about N-acetyl-9-(2,3,5-tri-O-acetylpentofuranosyl)-9H-purin-6-amine 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: 78.0%

N6-Acetyladenine (6034-68-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → 6-N-2',3',5'-tri-O-tetraacetyladenosine (7387-58-8,80007-24-5)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201003648

Reference yield: 50.0%

acetic anhydride (108-24-7) + adenosine (58-61-7) → 6-N-2',3',5'-tri-O-tetraacetyladenosine (7387-58-8,80007-24-5) + triacetyladenosine (7387-57-7,953089-09-3)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 24h; Cooling with ice;

DOI:10.1039/b716151d

Reference yield: 68.0%

6-N-2',3',5'-tri-O-tetraacetyladenosine (7387-58-8,80007-24-5) + benzyl bromide (100-39-0) → 1-N-benzyl-N6-acetyl-2',3',5'-tri-O-acetyladenosine

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In acetonitrile; at 65 ℃; for 12h; Reagent/catalyst; regioselective reaction;

DOI:10.1080/15257770.2015.1016169

upstream raw materials:

acetic anhydride

adenosine

N₆-Acetyladenine

1,2,3,5-tetraacetylribose

Downstream raw materials:

N⁶,O^2',3',5'-Tetramethyladenosine

triacetyladenosine

2-Methoxyadenosine

N⁶-methyladenosine

Refernces

• 1、 Wolf, Joern,Dombos, Valeska,Appel, Bettina,Mueller, Sabine. "Synthesis of guanosine 5′-conjugates and their use as initiator molecules for transcription priming". supporting information; experimental part. p. 899 - 907. Retrieved 2008/10/09.