5'-Chloro-5'-deoxyadenosine

Base Information

• Chemical Name: 5'-Chloro-5'-deoxyadenosine
• CAS No.: 892-48-8
• Molecular Formula: C10H12ClN5O3
• Molecular Weight: 285.69
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10875948
• Nikkaji Number: J385.403E
• Wikidata: Q27120769
• Metabolomics Workbench ID: 56765
• ChEMBL ID: CHEMBL404658
• Mol file: 892-48-8.mol

Synonyms:5'-chloro-5'-deoxyadenosine;5'-deoxy-5'-chloroadenosine

Chemical Property of 5'-Chloro-5'-deoxyadenosine

Chemical Property:

• Vapor Pressure: 1.5E-17mmHg at 25°C
• Melting Point: 187 °C
• Refractive Index: 1.87
• Boiling Point: 645.6 °C at 760 mmHg
• PKA: 13.03±0.70(Predicted)
• Flash Point: 344.2 °C
• PSA: 119.31000
• Density: 2.03g/cm³
• LogP: -0.15230
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Water (Slightly, Heated)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 285.0628670
• Heavy Atom Count: 19
• Complexity: 338

Purity/Quality:

98%, ^*data from raw suppliers

5'-Chloro-5'-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CCl)O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CCl)O)O)N
• Uses: 5''-Deoxy-5''-chloroadenosine is an intermediate in the synthesis of 5''-Deoxy-5''-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

Technology Process of 5'-Chloro-5'-deoxyadenosine

There total 11 articles about 5'-Chloro-5'-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%

5'-chloro-5'-deoxy-2',3'-O-sulfinyladenosine (662131-88-6) → 5'-deoxy-5'-chloroadenosine (892-48-8)

Guidance literature:

With methanol; water; at 20 ℃;

DOI:10.1002/ejoc.200300435

Reference yield: 94.0%

5'-chloro-5'-deoxy-2',3'-O-sulphinyladenosine hydrochloride (69260-62-4) → 5'-deoxy-5'-chloroadenosine (892-48-8)

Guidance literature:

With ammonium hydroxide; In methanol; water; for 0.5h; Ambient temperature;

DOI:10.1139/v91-217

Reference yield: 91.0%

adenosine (58-61-7) → 5'-deoxy-5'-chloroadenosine (892-48-8)

Guidance literature:

With pyridine; thionyl chloride; In acetonitrile; at 0 - 20 ℃;

DOI:10.1002/anie.201606722

upstream raw materials:

5'-chloro-5'-deoxy-2',3'-O-sulfinyladenosine

5'-chloro-5'-deoxy-2',3'-O-sulphinyladenosine hydrochloride

9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

adenosine

Downstream raw materials:

5'-[3-(amino)propylthio]-5'-deoxyadenosine

2',3'-Di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine

2',3'-di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl>adenosine

5'-Fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine

Refernces

• 1、 Smil, David,Eram, Mohammad S.,Li, Fengling,Kennedy, Steven,Szewczyk, Magdalena M.,Brown, Peter J.,Barsyte-Lovejoy, Dalia,Arrowsmith, Cheryl H.,Vedadi, Masoud,Schapira, Matthieu. "Discovery of a dual PRMT5-PRMT7 inhibitor". . p. 408 - 412. Retrieved 2015.
• 2、 Sun, Huihua,Yeo, Wan Lin,Lim, Yee Hwee,Chew, Xinying,Smith, Derek John,Xue, Bo,Chan, Kok Ping,Robinson, Robert C.,Robins, Edward G.,Zhao, Huimin,Ang, Ee Lui. "Directed Evolution of a Fluorinase for Improved Fluorination Efficiency with a Non-native Substrate". . p. 14277 - 14280. Retrieved 2016.
• 3、 Atdjian, Colette,Braud, Emmanuelle,Coelho, Dylan,Ethève-Quelquejeu, Mélanie,Iannazzo, Laura. "Synthesis of triazole-linked SAM-adenosine conjugates: Functionalization of adenosine at N-1 or N-6 position without protecting groups". . . Retrieved 2020/08/07.
• 4、 McKean, Iain J. W.,Sadler, Joanna C.,Cuetos, Anibal,Frese, Amina,Humphreys, Luke D.,Grogan, Gideon,Hoskisson, Paul A.,Burley, Glenn A.. "S-Adenosyl Methionine Cofactor Modifications Enhance the Biocatalytic Repertoire of Small Molecule C-Alkylation". supporting information. p. 17583 - 17588. Retrieved 2019/11/11.