N6-Benzoyl-2'-deoxyadenosine

Base Information

• Chemical Name: N6-Benzoyl-2'-deoxyadenosine
• CAS No.: 4546-72-9
• Molecular Formula: C17H17N5O4
• Molecular Weight: 355.353
• Hs Code.: 29349990
• European Community (EC) Number: 224-903-6
• DSSTox Substance ID: DTXSID80196516
• Nikkaji Number: J297.809A
• Wikidata: Q72440252
• Mol file: 4546-72-9.mol

Synonyms:N6-Benzoyl-2'-deoxyadenosine;4546-72-9;305808-19-9;N-Benzoyl-2'-deoxyadenosine;N-Benzoyl-2'-deoxy-adenosine;N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide;N-Benzoyldeoxyadenosine;C17H17N5O4;EINECS 224-903-6;N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide;Adenosine, N -benzoyl-2'-deoxy-;6-n-benzoyldeoxyadenosine;N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)-9H-purin-6-yl)benzamide;SCHEMBL264408;6-N-benzoyl-2'-deoxyadenosine;N6 -benzoyl-2'-deoxyadenosine;N6-Benzoyl-2\'-deoxyadenosine;Adenosine, N-benzoyl-2'-deoxy-;DTXSID80196516;AMY31044;HG1037;MFCD00009628;AKOS015999137;CS-W011841;AC-32160;BP-58689;DS-14590;B3101;A826809;N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-oxolanyl]-6-purinyl]benzamide;N-[9-[(2R,4S,5R)-5-(hydroxymethyl)-4-oxidanyl-oxolan-2-yl]purin-6-yl]benzamide

Chemical Property of N6-Benzoyl-2'-deoxyadenosine

Chemical Property:

• Melting Point: 120-122°C
• PKA: 7.87±0.43(Predicted)
• PSA: 122.39000
• Density: 1.61 g/cm³
• LogP: 0.79230
• Storage Temp.: Store at 0°C
• Water Solubility.: Soluble in water (slightly), and methanol (20 mg/ml).
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 355.12805404
• Heavy Atom Count: 26
• Complexity: 504

Purity/Quality:

98%, ^*data from raw suppliers

N6-Benzoyl-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)C4=CC=CC=C4)CO)O
• Description: N-Benzoyl-2'-deoxyadenosine is a nucleoside analog that is used in the diagnosis of infections caused by bacteria. N-Benzoyl-2'-deoxyadenosine binds to DNA duplexes and alters their structure, which can be detected using electrophoresis. N-Benzoyl-2'-deoxyadenosine has been shown to have low bioavailability and is insoluble in water, so it must be administered intravenously. It has also been found to have anti-inflammatory properties, which may be due to its ability to inhibit prostaglandin synthesis.
• Uses: Reactant in the synthesis of 2', 5'-Dideoxycytidines and Other Derivatives of 2'-Deoxycytidine. Reactant in the synthesis of Mono- and Diamino Analogues of 2?-Deoxyadenosine, Cordycepin, 9-(3-Deoxy-α-D-Threo-Pentofuranosyl)-Adenine and 9-(2-Deoxy-α-D-Threo-Pentofuranosyl)Adenine.

Technology Process of N6-Benzoyl-2'-deoxyadenosine

There total 19 articles about N6-Benzoyl-2'-deoxyadenosine 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%

N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine (64723-02-0) → N6-benzoyl-2'-deoxyadenosine (4546-72-9)

Guidance literature:

With sodium hydroxide; In pyridine; methanol; for 0.01h; microwave irradiation;

DOI:10.1081/NCN-120006833

Reference yield: 97.0%

N-benzoyldeoxyadenosine 5'-(3'',5''-dimethoxybenzoin)carbonate (167872-05-1) → N6-benzoyl-2'-deoxyadenosine (4546-72-9)

Guidance literature:

In benzene; for 1h; Irradiation;

DOI:10.1021/jo00110a011

Reference yield: 96.0%

5'-O-(9-phenylthioxanthyl)-N6-benzoyl-2'-deoxyadenosine (253277-01-9) → N6-benzoyl-2'-deoxyadenosine (4546-72-9)

Guidance literature:

In water; acetonitrile; Irradiation;

DOI:10.1016/S0040-4039(99)01563-4

upstream raw materials:

N-benzoyl-3',5'-di-O-benzoyl-2'-deoxyadenosine

N⁶-benzoyl-5’-O-trityl-2’-deoxyadenosine

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

benzoyl chloride

Downstream raw materials:

α-deoxyadenosine

N⁶,2',3',5'-tetra-O-benzoyladenosine

N⁶-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine

N⁶-benzoyl-9-[3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine

Refernces

• 1、 Woell, Dominik,Smirnova, Julia,Galetskaya, Marina,Prykota, Tamara,Buehler, Jochen,Stengele, Klaus-Peter,Pfleiderer, Wolfgang,Steiner, Ulrich E.. "Intramolecular sensitization of photocleavage of the photolabile 2-(2-nitrophenyl)propoxycarbonyl (NPPOC) protecting group: Photoproducts and photokinetics of the release of nucleosides". experimental part. p. 6490 - 6497. Retrieved 2009/09/06.
• 2、 Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh S.. "Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters". . p. 5045 - 5048. Retrieved 2007/10/03.