Adenosine, 8-bromo-, 2',3',5'-triacetate

Base Information

• Chemical Name: Adenosine, 8-bromo-, 2',3',5'-triacetate
• CAS No.: 31281-86-4
• Molecular Formula: C16H18 Br N5 O7
• Molecular Weight: 472.252
• Mol file: 31281-86-4.mol

Synonyms:NSC 79212;EINECS 250-543-4;Adenosine, 8-bromo-, 2',3',5'-triacetate;SCHEMBL1096927

Chemical Property of Adenosine, 8-bromo-, 2',3',5'-triacetate

Chemical Property:

• Melting Point: 188-189 °C
• Boiling Point: 635°Cat760mmHg
• PKA: 2.80±0.10(Predicted)
• Flash Point: 337.8°C
• PSA: 157.75000
• Density: 1.85g/cm³
• LogP: 1.07610
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 471.03896
• Heavy Atom Count: 29
• Complexity: 655

Purity/Quality:

97% ^*data from raw suppliers

8-Bromo-2’,3’,5’-tri-O-acetyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C3=NC=NC(=C3N=C2Br)N)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1C(C([C@@H](O1)N2C3=NC=NC(=C3N=C2Br)N)OC(=O)C)OC(=O)C

Technology Process of Adenosine, 8-bromo-, 2',3',5'-triacetate

There total 4 articles about Adenosine, 8-bromo-, 2',3',5'-triacetate 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: 98.0%

triacetyladenosine (7387-57-7,953089-09-3) → 2',3',5'-tri-O-acetyl-8-bromoadenosine (31281-86-4)

Guidance literature:

With disodium hydrogenphosphate; bromine; In 1,4-dioxane; for 0.25h; Ambient temperature;

DOI:10.3987/COM-92-S20

Reference yield: 76.0%

acetic anhydride (108-24-7) + 8-bromoadenosine (2946-39-6) → 2',3',5'-tri-O-acetyl-8-bromoadenosine (31281-86-4)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 36h;

DOI:10.1021/ml500343r

Reference yield: 36.0%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(8-bromo-6-dimethylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (80585-35-9) → Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(8-bromo-6-methylamino-purin-9-yl)-tetrahydro-furan-3-yl ester (80585-38-2) + 2',3',5'-tri-O-acetyl-8-bromoadenosine (31281-86-4)

Guidance literature:

With potassium permanganate; In water; acetic acid; at 40 ℃; for 0.17h;

DOI:10.1016/S0040-4039(01)81864-5

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(8-bromo-6-dimethylamino-purin-9-yl)-tetrahydro-furan-3-yl ester

triacetyladenosine

acetic anhydride

8-bromoadenosine

Downstream raw materials:

2',3',5'-tri-O-acetyl-8-phenyladenosine

C₃₉H₄₀N₁₀O₁₂

8-Butylaminoadenosine

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(8-cyclohexyl-6-(cyclohexylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate