N2-ACETYL-O6-(DIPHENYLCARBAMOYL)GUANINE

Base Information

• Chemical Name: N2-ACETYL-O6-(DIPHENYLCARBAMOYL)GUANINE
• CAS No.: 112233-74-6
• Molecular Formula: C20H16 N6 O3
• Molecular Weight: 388.385
• Mol file: 112233-74-6.mol

Synonyms:Carbamicacid, diphenyl-, 2-(acetylamino)-1H-purin-6-yl ester (9CI);N2-Acetyl-O6-(diphenylcarbamoyl)guanine; N2-Acetyl-O6-diphenylcarbamoylguanine

Chemical Property of N2-ACETYL-O6-(DIPHENYLCARBAMOYL)GUANINE

Chemical Property:

• PKA: 6.13±0.40(Predicted)
• PSA: 113.10000
• Density: 1.41±0.1 g/cm3(Predicted)
• LogP: 3.72140
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

N2-Acetyl-O6-diphenylcarbamoylguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N2-Acetyl-O6-diphenylcarbamoylguanine is a reactant in the synthesis of 1'',2''-oxetane-nucleosides bearing 2''-C-Me substituents with anti-HCV activity.

Technology Process of N2-ACETYL-O6-(DIPHENYLCARBAMOYL)GUANINE

There total 8 articles about N2-ACETYL-O6-(DIPHENYLCARBAMOYL)GUANINE 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: 92.0%

diphenylcarbamic chloride (83-01-2) + 2,9-diacetylguanine (3056-33-5) → N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In pyridine; for 1h; Ambient temperature;

DOI:10.1021/jo9617023

Reference yield: 82.0%

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + acetic anhydride (108-24-7) + diphenylcarbamic chloride (83-01-2) → N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6)

Guidance literature:

2-amino-1,9-dihydro-6H-purin-6-one; acetic anhydride; In N,N-dimethyl acetamide; at 160 ℃; for 6.5h; Inert atmosphere;

diphenylcarbamic chloride; With pyridine; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 1h;

In ethanol; water; at 95 ℃; for 2h;

DOI:10.1021/jacs.7b02988

Reference yield: 70.0%

N-(6-oxo-5,9-dihydro-6H-purin-2-yl)acetamide + diphenylcarbamic chloride (83-01-2) → N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6)

Guidance literature:

With pyridine; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201903400

upstream raw materials:

diphenylcarbamic chloride

2,9-diacetylguanine

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

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

Downstream raw materials:

2-(N-acetyl)-6-(O-diphenylcarbamoyl)-9-vinylguanine

N²-acetyl-9-(2',3',5'-tri-O-acetyl-β-L-ribofuranosyl)-6-O-diphenylcarbamoylguanine

ethyl 3-(2-N-acetyl-6-O-(diphenylcarbamoyl)guanin-9-ylmethyl)-2-(hydroxymethyl)propanoate

2'-O-acetyl-5'-azido-3'-[2-(tert-butyldiphenylsilanyloxy)ethyl]-3',5'-dideoxy-2-N-acetyl-6-O-diphenylcarbamoylguanosine

Refernces

• 1、 Wamberg, Michael C.,Pedersen, Pernille L.,L?ffler, Philipp M. G.,Albertsen, Anders N.,Maurer, Sarah E.,Nielsen, Kent A.,Monnard, Pierre-Alain. "Synthesis of Lipophilic Guanine N-9 Derivatives: Membrane Anchoring of Nucleobases Tailored to Fatty Acid Vesicles". . p. 1893 - 1905. Retrieved 2017.
• 2、 Levinson, Adam M.,McGee, John H.,Roberts, Andrew G.,Creech, Gardner S.,Wang, Ting,Peterson, Michael T.,Hendrickson, Ronald C.,Verdine, Gregory L.,Danishefsky, Samuel J.. "Total Chemical Synthesis and Folding of All- l and All- d Variants of Oncogenic KRas(G12V)". supporting information. p. 7632 - 7639. Retrieved 2017/06/13.