2'-Deoxy-7,8-dihydro-8-oxoadenosine

Base Information

• Chemical Name: 2'-Deoxy-7,8-dihydro-8-oxoadenosine
• CAS No.: 62471-63-0
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.244
• DSSTox Substance ID: DTXSID20904172
• Mol file: 62471-63-0.mol

Synonyms:2'-deoxy-7,8-dihydro-8-oxoadenosine;8-oxo-2'-deoxyadenosine;8-oxo-7,8-dihydro-2'-deoxyadenosine;8-oxo-dA;8-oxo-dAdo

Chemical Property of 2'-Deoxy-7,8-dihydro-8-oxoadenosine

Chemical Property:

• PKA: 10.37±0.20(Predicted)
• PSA: 139.54000
• Density: 1.672±0.06 g/cm3(Predicted)
• LogP: -0.66400
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

97% ^*data from raw suppliers

8-Oxo-2’-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C3=NC=NC(=C3NC2=O)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](OC1N2C3=NC=NC(=C3NC2=O)N)CO)O
• Uses: 8-Oxo-2’-deoxyadenosine is the first example of a native DNA lesion that stabilizes human telomeric G-quadruplex DNA.

Technology Process of 2'-Deoxy-7,8-dihydro-8-oxoadenosine

There total 10 articles about 2'-Deoxy-7,8-dihydro-8-oxoadenosine 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: 50.0%

8-bromo-2'-deoxyadenosine (14985-44-5,90968-89-1) + 2-hydroxyethanethiol (60-24-2) → (2R,3S,5R)-5-[6-Amino-8-(2-hydroxy-ethylsulfanyl)-purin-9-yl]-2-hydroxymethyl-tetrahydro-furan-3-ol (876380-66-4) + 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 8-bromoadenine (6974-78-3)

Guidance literature:

With triethylamine; In methanol; for 7h; Heating;

DOI:10.1016/j.tetlet.2005.11.099

Reference yield:

duplex AQ-5'-UUUUAAUUAAUUAAUUAAUAUAUUT-3'*3'-AAAATTAATTAATTAATTATATAAA-5', AQ = 2-anthraquinonecarboxamide-N-(2-ethyl) group → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 2'-deoxy-5-(hydroxymethyl)uridine (5116-24-5,15425-01-1,143156-50-7) + trans-5'-carboxy-5,6-dihydroxy-5,6-dihydro thymidine (38645-24-8) + (+)-cis-(5S,6R)-5,6-dihydroxy-5,6-dihydrothymidine (38709-52-3) + 5-formyl-2'-deoxyuridine (4494-26-2)

Guidance literature:

duplex AQ-5'-UUUUAAUUAAUUAAUUAAUAUAUUT-3'*3'-AAAATTAATTAATTAATTATATAAA-5', AQ = 2-anthraquinonecarboxamide-N-(2-ethyl) group; With air; at 30 ℃; for 0.25h; pH=7.0; Irradiation; aq. phosphate buffer;

Time; Mechanism; Reactivity; aq. buffer; Enzymatic reaction;

DOI:10.1039/b717437c

Reference yield:

3,4-dihydroxy-1,3,5-(10),6,8-estrapentaen-17-one → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; In phosphate buffer; at 37 ℃; for 3h; pH=7.4; Further Variations:; Reagents; Product distribution;

DOI:10.1021/tx980083l

upstream raw materials:

1,6-Hexanediamine

8-bromo-2'-deoxyadenosine

2-hydroxyethanethiol

2'-deoxy-D-adenosine

Downstream raw materials:

5'-KP-8-oxodA

3'-O-tert-butyldimethylsilyl-7,8-dihydro-8-oxodeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate]

N-(4-benzyloxy-3,5-dibromobenzyl)-2'-deoxy-8-oxoadenosine

N-(4-benzyloxy-3,5-dibromobenzyl)-8-oxoadenine