2-Bromo-2',3',5'-tri-O-acetylinosine

Base Information

• Chemical Name: 2-Bromo-2',3',5'-tri-O-acetylinosine
• CAS No.: 41623-91-0
• Molecular Formula: C16H17BrN4O8
• Molecular Weight: 473.237
• Mol file: 41623-91-0.mol

Synonyms:2-Bromo-2',3',5'-tri-O-acetylinosine;

Chemical Property of 2-Bromo-2',3',5'-tri-O-acetylinosine

Chemical Property:

• PSA: 151.96000
• LogP: 0.61830
• Solubility.: Chloroform, Dichloromethane, Dimethyl Sulfoxide

Purity/Quality:

97% ^*data from raw suppliers

2-Bromo-2'',3'',5''-tri-O-acetylinosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Bromo-2',3',5'-tri-O-acetylinosine

There total 8 articles about 2-Bromo-2',3',5'-tri-O-acetylinosine 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:

2-Bromo-9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purine + 1,2,3,5-tetraacetylribose (13035-61-5) → 2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine (41623-91-0) + Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-bromo-6-oxo-1,6-dihydro-purin-7-yl)-tetrahydro-furan-3-yl ester (87782-02-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 0.25h; Yield given. Yields of byproduct given; Heating;

DOI:10.1021/jm00368a012

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester (127218-16-0) → 2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine (41623-91-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; Yield given;

DOI:10.1039/c39890001769

Reference yield:

2-bromo-1,9-dihydro-6H-purin-6-one (87781-93-9) → 2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)hypoxanthine (41623-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Et₃N; 2.) PPh₃, diethyl azodicarboxylate; 3.) 80 percent HOAc / 1.) 100 deg C, 2 h; 2.) dioxane, 80 deg C, 6 h; 3.) 80 deg C

3: 95 percent / CF₃SO₃SiMe₃ / acetonitrile / reflux, 1h; rt, 16 h

4: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile

With trimethylsilyl trifluoromethanesulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; diethylazodicarboxylate; In acetonitrile;

DOI:10.1039/c39890001769

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2-bromo-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-3-yl ester

1,2,3,5-tetraacetylribose

2-bromo-1,9-dihydro-6H-purin-6-one

2-bromo-6-(4-nitrophenylethoxy)purine

Downstream raw materials:

O^2'_,O3'_,O5'-triacetyl-N²-phenyl-guanosine

N²-(p-n-butylphenyl)-9-β-D-ribofuranosylguanine

Imidazole-1-carbothioic acid O-{(2R,3R,3aR,9aR)-2-[2-(4-butyl-phenylamino)-6-oxo-1,6-dihydro-purin-9-yl]-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl} ester

N²-(p-n-butylphenyl)-2'-deoxyguanosine 5'-triphosphate

Refernces

• 1、 Wright, George E.,Dudycz, Lech W.. "Synthesis and Characterization of N2-(p-n-Butylphenyl)-2'-deoxyguanosine and Its 5'-Triphosphate and Their Inhibition of HeLa DNA Polymerase α". . p. 175 - 181. Retrieved 2007/10/02.