N6-Benzoyladenine

Base Information

• Chemical Name: N6-Benzoyladenine
• CAS No.: 4005-49-6
• Molecular Formula: C12H9N5O
• Molecular Weight: 239.236
• Hs Code.: 29335990
• European Community (EC) Number: 629-048-6
• NSC Number: 98641
• UNII: 7BQB2WI1II
• DSSTox Substance ID: DTXSID90193112
• Nikkaji Number: J715.610C
• ChEMBL ID: CHEMBL525721
• Mol file: 4005-49-6.mol

Synonyms:N6-benzoyladenine

Chemical Property of N6-Benzoyladenine

Chemical Property:

• Appearance/Colour: White crystal
• Melting Point: 242-244 °C
• Refractive Index: 1.76
• Boiling Point: 443.7 °C at 760 mmHg
• PKA: 11.98±0.20(Predicted)
• Flash Point: 222.2 °C
• PSA: 83.56000
• Density: 1.491 g/cm³
• LogP: 1.67820
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 239.08070993
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

98%, ^*data from raw suppliers

N6-Benzoyladenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=NC=NC3=C2NC=N3
• Uses: N-Benzoylaminopurine is used in the organic synthesis of adenine derivative molecules such as bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine and to produce oxy-peptide nucleic acids. N6-Benzoyladenine is used in the organic synthesis of adenine derivative molecules such as bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine and to produce oxy-peptide nucleic acids.

Technology Process of N6-Benzoyladenine

There total 28 articles about N6-Benzoyladenine 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: 90.3%

benzoyl chloride (98-88-4) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → N-benzoyladenine (4005-49-6)

Guidance literature:

With pyridine; at 60 ℃;

DOI:10.1016/j.bmc.2017.06.032

Reference yield: 87.0%

N-[9-((3aR,4R,6aS)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide (152387-33-2) → N-benzoyladenine (4005-49-6) + (4S,5R)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Guidance literature:

With methanol; triethylamine; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73866-4

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + benzoic acid (65-85-0,8013-63-6) → N-benzoyladenine (4005-49-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 100 - 130 ℃;

DOI:10.1248/cpb.c16-00410

upstream raw materials:

benzoyl chloride

7H-purin-6-ylamine

benzoic acid anhydride

adenine

Downstream raw materials:

6-benzylaminopurine

1',2',3'-Trideoxy-4'-O-benzoyl-3'-(N-6-benzoyl-9-adenyl)-D-threo-pent-1'-enopyranose

N-6-Benzoyl-9-(2'-deoxy-3',4'-di-O-benzoyl-β-D-ribopyranosyl)adenine

Benzoic acid (S)-4-(6-benzoylamino-purin-9-yl)-3,4-dihydro-2H-pyran-3-yl ester

Refernces

The adenine derivative of α-L-LNA (α-L-ribo configured locked nucleic acid): Synthesis and high-affinity hybridization towards DNA, RNA, LNA and α-L-LNA complementary sequences

10.1016/S0960-894X(01)00110-X

The research focuses on the synthesis and hybridization properties of a 9-mer adenine derivative of α-L-LNA (α-L-ribo configured locked nucleic acid), which is a type of nucleic acid mimic designed to have superior properties such as increased stability towards nucleolytic degradation and enhanced binding affinity and specificity towards complementary nucleic acid targets. The study successfully developed a synthetic route for the first α-L-LNA purine monomer, involving the synthesis of a bicyclic adenine nucleoside through a condensation reaction between l-threo-pentofuranose derivative and 6-N-benzoyladenine, followed by C20-epimerization and cyclization. The synthesized α-L-LNA monomers were then incorporated into a 9-mer oligonucleotide, which demonstrated high-affinity hybridization with complementary DNA, RNA, LNA, and α-L-LNA target sequences. The chemicals used in the process included 6-N-benzoyladenine, SnCl4, TMS-triflate, N,O-bis(trimethylsilyl)acetamide, mesyl chloride, sodium hydride, and various other reagents for protection, deprotection, and purification steps. The conclusions of the research were that the α-L-LNA monomers, particularly the adenine derivatives, significantly enhance the affinity of the resulting oligonucleotides for their complementary sequences, and that α-L-LNA:α-L-LNA and α-L-LNA:LNA duplexes form exceptionally stable structures, comparable to LNA:LNA duplexes.

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