2'-O-acetyladenosine

Base Information

• Chemical Name: 2'-O-acetyladenosine
• CAS No.: 6554-28-5
• Molecular Formula: C12H15N5O5
• DSSTox Substance ID: DTXSID30573131
• Wikidata: Q82461722
• Mol file: 6554-28-5.mol

Synonyms:2'-O-acetyladenosine;O-acetyl-adenosine;SCHEMBL9186652;DTXSID30573131

Chemical Property of 2'-O-acetyladenosine

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 309.10731860
• Heavy Atom Count: 22
• Complexity: 427

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC1N2C=NC3=C(N=CN=C32)N)CO)O
• Isomeric SMILES: CC(=O)O[C@@H]1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)CO)O

Technology Process of 2'-O-acetyladenosine

There total 3 articles about 2'-O-acetyladenosine 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:

vinyl acetate (108-05-4,9003-20-7) + adenosine (58-61-7) → 2'-O-acetyladenosine (6554-28-5) + 3'-O-Acetyl-adenosin (6554-21-8)

Guidance literature:

With PSL; In tetrahydrofuran; at 60 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(00)00222-2

Reference yield:

acetic anhydride (108-24-7) + adenosine (58-61-7) → 2'-O-acetyladenosine (6554-28-5) + 3'-O-Acetyl-adenosin (6554-21-8)

Guidance literature:

With Candida Cyclindracea lipase; In tert-butyl alcohol; at 37 ℃; for 8h; Reagent/catalyst; Overall yield = 83 %; regioselective reaction; Enzymatic reaction;

Reference yield:

N,O-diacetyl-4-stilbenylhydroxylamine (26594-44-5,26488-34-6) + adenosine (58-61-7) → 2'-O-acetyladenosine (6554-28-5) + 3'-O-Acetyl-adenosin (6554-21-8)

Guidance literature:

In acetone; at 37 ℃; Product distribution; other nucleoside; phosphate buffer (pH 7.4); var. acetylarylhydroxylamines;

DOI:10.1021/jo00137a021

upstream raw materials:

N,O-diacetyl-4-stilbenylhydroxylamine

adenosine

vinyl acetate

acetic anhydride